6-bromoimidazo[1,5-a]pyridine

To a mixture of N-((5-bromopyridin-2- yl)methyl)formamide (1.0 g, 4.6 mmol) in toluene (30 mL) was added POCI3 (1.0 mL, 10.9 mmol). The mixture was stirred at 103°C for 2 hr then concentrated to dryness. The residue was dissolved in DCM, washed in sequence with saturated aqueous NaHCCh and brine, dried over anhydrous Na2SC>4 and concentrated under reduced pressure. The residue was purified by flash column chromatography to give the desired product (0.5 g, 55percent yield) as yellow solid. LC-MS: m/z 197, 199 (M+H)+.Neat POClSynthesis of To a mixture of AICI3 (798 mg, 6.0 mmol) in dry DCM (12 mL) at 0C was added dropwise acetyl chloride (471 mg, 6.0 mmol). The mixture was stirred at 0C for 10 min, followed by dropwise addition of a solution of 6- bromoimidazo[l, 5-a]pyridine (400 mg, 2.0 mmol) in dry DCM (3 mL). The resulting mixture was stirred at 0C for 0.5 hr then poured into ice -water (20 g) and extracted with DCM. The combined organic layers were washed with brine, dried over anhydrous Na2SC>4, and concentrated under reduced pressure. The residue was purified by flash column chromatography to give the desired product (130 mg, 27% yield) as a yellow solid. LC-MS: m/z 239, 241 (M+H)+.tert.-Butyl imidazo[1, 5-a]pyridin-6-ylcarbamate Under argon, a microwave vessel was charged with 200 mg (1.02 mmol) of

Molecular Weight:197.03
XLogP3:2.5
Hydrogen Bond Acceptor Count:1
Exact Mass:195.96361
Monoisotopic Mass:195.96361
Topological Polar Surface Area:17.3
Heavy Atom Count:10
Complexity:129
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes