8-BROMO-IMIDAZO[1,2-A]PYRIDINE

2-Amino-3-bromopyridine (VII-41) (5.00 g, 28.9 mmol) was dissolved in ethanol (100 mL), sodium hydrogencarbonate (3.64 g, 43.3 mmol) and 2-chloroacetaldehyde (7.1 mL, 43 mmol) were added, and the mixture was stirredunder refluxing with heating for 4 hr. The mixture was allowed to cool, and the solvent was evaporated under reducedpressure. Water was added, and the mixture was extracted with ethyl acetate. The organic layer was washed withsaturated brine, dried over anhydrous sodium sulfate, and filtered. The solvent was evaporated under reduced pressure.The residue was purified by silica gel column chromatography (n-hexane:ethyl acetate = 70:30 → 40:60) to give 8-bromoimidazo[1, 2-a]pyridine (VII-42) (yield 5.71 g, quantitative2-Amino-3-bromopyridine (VII-41) (5.00 g, 28.9 mmol) was dissolved in ethanol (100 mL)Sodium hydrogencarbonate (3.64 g, 43.3 mmol)And 2-chloroacetaldehyde (7.1 mL, 43 mmol), and the mixture was stirred under reflux heating for 4 hours.After standing to cool, under reduced pressure, the solvent was distilled off, Water was added and extracted with ethyl acetate.The organic layer was washed with saturated brine, Dried over anhydrous sodium sulfate, and filtered.The solvent was distilled off under reduced pressure.The residue was purified by silica gel column chromatography (n-hexane: ethyl acetate = 70: 30 → 40: 60)To give 8-bromoimidazo [1, 2-a] pyridine (VII-42)(Yield 5.71 g, yield quantitative)Was obtained.To a solution of Preparation 277: N-(2-((tert-butyldimethylsilyl)oxy)-1-(imidazo[1 , 2-a]pyridin-8-yl)ethyl)-2- methylpropane-2-sulfinamide (1975) (1976) AT-BuLi (2.5 M in hexanes, 0.216 mL, 0.541 mmol) was added dropwise to a solution of 8- bromoimidazo[1 , 2-a]pyridine (97 mg, 0.491 mmol) in dry THF (2 mL) at -78C and the mixture was stirred for 1 h before (£)-N-(2-((tert-butyldimethylsilyl)oxy)ethylidene)-2-methylpropane-2- sulfinamide (150 mg, 0.541 mmol) in THF (0.5 mL) was added. The reaction mixture was stirred at -78C for 1 h, then warmed to rt and stirred for 1 h. The reaction was quenched with sat. NH4CI (aq.) (30 mL) and left to stand overnight. The mixture was extracted with ethyl acetate (3 x 30 mL) and the combined organic extracts were washed with brine (30 mL), dried (MgSCU), filtered and concentrated in vacuo to give a yellow oil. The residue was purified by (1977) chromatography (S1O2, 12 g column, 0 to 6% of MeOH in DCM) to afford the title compound (82 mg, 38%) as a colourless solid. LCMS: [M+H]+ = 396.To a 0.5 - 2 mL microwave vial was added rac-1-(2S, 3R, 4R)-4-amino-2, 3-dimethyl-3, 4- dihydroquinolin-1(2H)-yl)ethanone (for a preparation see Intermediate 6, 40 mg, 0.183 mmol), DavePhos (7 mg, 0.018 mmol), Pd2(dba)3 (17 mg, 0.019 mmol), sodium tert-butoxide (26.4 mg, 0.275 mmol) and

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