Methyl iodide → Methyl 5-bromo-1-methyl-1H-pyrazolo[3,4-B]pyridine-3-carboxylate

HRID 1982942Notes

Reaction equation

[H-].[Na+].[CH3:3][O:4][C:5]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([Br:16])[CH:14]=2)[NH:9][N:8]=1)=[O:6].[CH3:17]I>C1COCC1>[CH3:3][O:4][C:5]([C:7]1[C:15]2[C:10](=[N:11][CH:12]=[C:13]([Br:16])[CH:14]=2)[N:9]([CH3:17])[N:8]=1)=[O:6]

Participants

Conditions

Temperature: 0 °C

Procedure

Sodium hydride (47 mg, 60% in mineral oil, 1.18 mmol) was added in portions to a solution of 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid methyl ester Compound 1b (0.3 g, 1.17 mmol) in dry THF (20 mL) at 0° C. The mixture was stirred at 0° C. for 15 minutes then methyl iodide (80 μl, 1.29 mmol) was added. The reaction was warmed to room temperature gradually and stirred overnight. the solvent was removed and the residue was purified by silica gel chromatography (10% to 50% of ethyl acetate in hexanes) to yield 5-bromo-1-methyl-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid methyl ester Compound 11a (0.31 g, 97% yield) as a white powder. 1H NMR (400 MHz, CDCl3) δ 9.89 (s, 2H), 4.51 (s, 3H), 3.37 (s, 3H); MS (ESI) m/z: 271 (M+H+).

Workup

temperatureThe reaction was warmed to room temperature gradually
stirringstirred overnight
customthe solvent was removed
customthe residue was purified by silica gel chromatography (10% to 50% of ethyl acetate in hexanes)

Sources & evidence

ORD record: ord-46ab2e7dd7bc4ac9919d91b81cf08d88
Source dataset: uspto-grants-2009_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07541367B2

Reaction notes

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