5-Bromo-3-methyl-7-azaindole

To a solution of 5-bromo-3-methyl-l-tosyl-lH-pyrrolo[2, 3-b]pyridine (35 g, 96.2 mmol) in methanol (200 mL) was added a solution of 6N sodium hydroxide (200 mL) and the mixture was heated at reflux for 2h. The reaction mixture was concentrated in vacuo to remove methanol and adjusted to pH 7 with citric acid. The resulting solid was filtered, washed with water, dried to afford 5-bromo-3-methyl-lH-pyrrolo[2, 3-b]pyridine as a yellow solid (20 g, 98.5percent): NMR (400MHz, DMSO-d6), δ 11.462 (s, 1H), 8.134 (s, 1H), 8.045 (s, 1 H), 7.210 (s, 1H), 2.135 (s, 3H).Step 6: 5-bromo-3-methyl-lH-pyrrolo[2, 3-b]pyridine To a solution of 5-bromo-3-methyl-l-tosyl-lH-pyrrolo[2, 3-b]pyridine (35 g, 96.2 mmol) in methanol (200 mL) was added a solution of 6N sodium hydroxide (200 mL) and the mixture was heated at reflux for 2h. The reaction mixture was concentrated in vacuo to remove methanol and adjusted to pH 7 with citric acid. The resulting solid was filtered, washed with water, dried to afford 5-bromo-3- methyl-lH-pyrrolo[2, 3-b]pyridine as a yellow solid (20 g, 98.5percent): H NMR (400MHz, DMSO-d6), δ 11.462 (s, 1H), 8.134 (s, 1H), 8.045 (s, 1 H), 7.210 (s, 1H), 2.135 (s, 3H).Preparation of 5-bromo-3-methyl-1H-pyrrolo[2, 3-b]pyridine (B-5-4)To a solution of 5-bromo-3-methyl-2-(trimethylsilyl)-1 H-pyrrolo[2, 3-b]pyridin (B-5-3) (5 g, 17.8 mmol) in THF (50 mL) was added 2 N HCI (20 ml_). The mixture was stirred at reflux overnight. HPLC showed the reaction was complete. After the mixture was concentrated under reduced pressure, the residue was dissolved in aqueous NaHCOTo a solution of 5-bromo-3-methyl-l-tosyl-lH-pyrrolo[2, 3-b]pyridine (35 g, 96.2 mmol) in methanol (200 mL) was added a solution of 6N sodium hydroxide (200 mL) and the mixture was heated at reflux for 2h. The reaction mixture was concentrated in vacuo to remove methanol and adjusted to pH 7 with citric acid. The resulting solid was filtered, washed with water, dried to afford 5-bromo-3-methyl-lH-pyrrolo[2, 3-b]pyridine as a yellow solid (20 g, 98.5percent): NMR (400MHz, DMSO-d6), δ 11.462 (s, 1H), 8.134 (s, 1H), 8.045 (s, 1 H), 7.210 (s, 1H), 2.135 (s, 3H).Step 6: 5-bromo-3-methyl-lH-pyrrolo[2, 3-b]pyridine To a solution of 5-bromo-3-methyl-l-tosyl-lH-pyrrolo[2, 3-b]pyridine (35 g, 96.2 mmol) in methanol (200 mL) was added a solution of 6N sodium hydroxide (200 mL) and the mixture was heated at reflux for 2h. The reaction mixture was concentrated in vacuo to remove methanol and adjusted to pH 7 with citric acid. The resulting solid was filtered, washed with water, dried to afford 5-bromo-3- methyl-lH-pyrrolo[2, 3-b]pyridine as a yellow solid (20 g, 98.5percent): H NMR (400MHz, DMSO-d6), δ 11.462 (s, 1H), 8.134 (s, 1H), 8.045 (s, 1 H), 7.210 (s, 1H), 2.135 (s, 3H).Preparation of 5-bromo-3-methyl-1H-pyrrolo[2, 3-b]pyridine (B-5-4)To a solution of 5-bromo-3-methyl-2-(trimethylsilyl)-1 H-pyrrolo[2, 3-b]pyridin (B-5-3) (5 g, 17.8 mmol) in THF (50 mL) was added 2 N HCI (20 ml_). The mixture was stirred at reflux overnight. HPLC showed the reaction was complete. After the mixture was concentrated under reduced pressure, the residue was dissolved in aqueous NaHCO

Molecular Weight:211.06
XLogP3:2.4
Hydrogen Bond Donor Count:1
Hydrogen Bond Acceptor Count:1
Exact Mass:209.97926
Monoisotopic Mass:209.97926
Topological Polar Surface Area:28.7
Heavy Atom Count:11
Complexity:151
Covalently-Bonded Unit Count:1
Compound Is Canonicalized:Yes