6-Bromo-3H-imidazo[4,5-b]pyridine

A solution of compound 217 (1.00 g, 5.32 mmol), formic acid (0.5 mL) and triethyl orthoformate (15 mL) were stirred at 100Preparative Example 23 Step 1: 6-bromo-3H-imidazo[4, 5-b]pyridine A solution of 5-bromopyridine-2, 3-diamine (10.0 g, 53.0 mmol) in formic acid (96percent, 100 mL) was heated to reflux for 10 h and subsequently concentrated to dryness in vacuo. The residue was taken up in water and the title compound was collected as a solid by filtration, washed with water (2 x 30 niL) and dried to afford 6-bromo-3H-imidazo[4, 5-b]pyridine (10.0 g, 95percent): H NMR (400 MHz, methanol-d4) δ 8.46 (s, 1H), 8.40 (s, 1H), 8.21 (s, 1H).Step 1: A solution of 5-bromo-pyridine-2, 3-diamine (3.0 g, 15.96 mmol) and HCOOH (1.1 mL) in triethoxymethane(48 mL) was stirred at 90 °C for 3 h. The reaction mixture was concentrated under reduced pressure. The residuewas purified by silica gel chromatography eluting with 40:1 DCM/MeOH to give 6-bromo- 3H-imidazo[4, 5-b]pyridine asa light brown solid (2.74 g, 86.7percent). 1H NMR (300 MHz, DMSO-d6) δ 8.49 (s, 1H), 8.44 (s, 1H), 8.30 (br s, 1H). LCMS(ESI) m/z 198 (M + H)+.Example 8; 6-(Tributylstannyl)-l-((2-(trimethylsilyl)ethoxy)methyl)-lH- imidazo[4, 5-b]pyridine 5046 47[00248] To 3.07 g of 5-bromo-2, 3-diaminopyridine 46 was added 20 mL formic acid under NExample 6a 6-(Tributylstannyl)-l-((2-(trimethylsilyl)ethoxy)methyl)-lH- imidazo[4, 5-b]pyridine 50[00289] To 3.07g of 5-bromo-2To a stirred solution of 5-Bromo-pyridine-2, 3-diamine (2g, 10.6mmol ) in triethyl orthoformate ( 10 ml) was added formic acid( 1 ml ) and the total reaction mass stirred at 100°C for 3h.Reaction mass was cooled to room temperature and concentrated under vacuum. Crude reaction mass was purified by eluting with 5percent methanol in dichloromethane to get the desired compound 2 (lg )Step-1 [0138] To a stirred solution of 5-Bromo-pyridine-2, 3-diamine (2 g, 10.6 mmol) in triethyl orthoformate (10 ml) was added formic acid (1 ml) and the total reaction mass stirred at 100° C. for 3 h. Reaction mass was cooled to room temperature and concentrated under vacuum. Crude reaction mass was purified by eluting with 5percent methanol in dichloromethane to get the desired compound 2 (1 g)

Molecular Weight:198.02
XLogP3:1.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:2
Exact Mass:196.95886
Monoisotopic Mass:196.95886
Topological Polar Surface Area:41.6
Heavy Atom Count:10
Complexity:130
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes