Product Name	N-(6-Bromoimidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoroacetamide
CAS Number	504413-35-8
Molecular Formula	C₉H₅BrF₃N₃O
Molecular Weight	308.06
SMILES Code	O=C(NC1=CN2C=C(Br)C=CC2=N1)C(F)(F)F
MDL No.	MFCD11976190
Pubchem ID	12065953
InChI Key	BUYPVRDWQVLXDL-UHFFFAOYSA-N

Synthesis Route

Synthesis：504413-35-8

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1005785-49-8		407-25-0		504413-35-8

Productivity	Synthesis conditions	Experimental procedures
96%	At 60℃; for 2 h;	Step 3. N-(6-Bromoimidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoroacetamide To a 250-mL round-bottom flask equipped with a reflux condenser was added 2-(5-bromo-2-(4-methylphenylsulfonamido)pyridin-1(2H)-yl)acetamide (10.0 g, 26.0 mmol), 1,2-dichloroethane (150 mL), and finally trifluoroacetic anhydride (18.4 mL, 130 mmol). The mixture was stirred at 60°C for 2 h. The solution was cooled to room temperature and concentrated. The resulting solid was dissolved in DCM (300 mL) and washed with 10% NaHCO₃ (2 × 100 mL). The aqueous washings were extracted with DCM (2 × 100 mL) and combined with the initial DCM solution. The combined solutions were washed with brine (100 mL), dried (Na2SO4) and concentrated to give the title compound as a tan solid which was used without further purification (7.72 g, 96%).
52%	Stage #1: Reflux Stage #2: With sodium hydrogencarbonate In water for 0.25 h;	Trifluoroacetic anhydride (24 mL) was slowly added to a stirred suspension of 2-[(2Z)-5-bromo-2-{[(4-methylphenyl)sulfonyl]imino}pyridin-1(2H)-yl]acetamide (4.8 g, 12.5 mmol) in anhydrous DCM (60 mL). After reflux for 3 hours, the reaction mixture was concentrated under reduced pressure, and the resulting yellow solid was suspended in saturated aqueous sodium bicarbonate solution, stirred for 15 minutes, and filtered. The crude product was purified by silica gel flash chromatography (PE:EtOAc, 90:10) to afford the title compound as a light yellow solid (2.0 g, 52%). HPLC, Rt: 3.4 min (purity: 97%). UPLC/MS, M+ (ESI): 308.1, 310.1, M- (ESI): 306.1, 308.1. 1 H-NMR (DMSO-d6, 400MHz) δ 12.53 (brs, 1H), 8.94 (m, 1H), 8.23 (s, 1H), 7.49 (m, 1H), 7.39 (m, 1H).

Chemical Properties

N-(6-Bromoimidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoroacetamide appears as a white to off-white crystalline powder.Its predicted density is 1.87±0.1 g/cm³,and the predicted pKa is 0.95±0.46.It is stable for storage when sealed in a dry environment at room temperature.The melting point is between 154 and 158°C.It has limited water solubility but dissolves readily in methanol,ethanol,THF,and DMF,with moderate solubility in ethyl acetate.The compound contains an electron-deficient imidazopyridine core,a bromine substituent,and a trifluoroacetamide group.The amide bond is stable under neutral conditions but can hydrolyze under prolonged exposure to strong acids or bases.The bromine is moderately reactive in cross-coupling reactions.

Description

N-(6-Bromoimidazo[1,2-a]pyridin-2-yl)-2,2,2-trifluoroacetamide(CAS No.504413-35-8)is a functionalized imidazo[1,2-a]pyridine,a privileged scaffold in medicinal chemistry.The structure features a bromine atom at the 6-position for further functionalization and a strong electron-withdrawing trifluoroacetamide group on the imidazole nitrogen,which modulates the electron density of the fused ring system.

Uses

1.Electron-Deficient Building Block for TADF Emitters
The strong electron-withdrawing trifluoroacetamide group makes this compound an ideal acceptor unit.It is coupled with donor units like carbazole or acridine via Buchwald-Hartwig amination at the bromine site to create donor-acceptor molecules exhibiting thermally activated delayed fluorescence(TADF)for efficient,low-cost OLED emitters.

2.Covalent Probe for Kinase Profiling
The bromine is replaced with a terminal alkyne via Sonogashira coupling,creating a"clickable"probe.This probe,bearing the imidazopyridine pharmacophore,is used in competitive activity-based protein profiling(ABPP)to identify and validate novel ATP-binding sites across the human kinome.

3.Monomer for Conjugated Microporous Polymers(CMPs)
Polymerized via Yamamoto or Sonogashira coupling reactions using the bromine site.The resulting CMPs possess high surface areas,permanent porosity,and excellent chemical stability,making them effective heterogeneous photocatalysts for organic transformations like aerobic oxidations and pollutant degradation under visible light.

4.Intermediate for Antiviral Nucleoside Analogs
The bromine undergoes Pd-catalyzed cyanation,and the resulting nitrile is reduced and cyclized to form a novel triazole-fused nucleobase analog.This analog is glycosylated to produce potential nucleoside reverse transcriptase inhibitors with activity against drug-resistant strains of HIV.