Diisopropylethylamine → HCID 178455430, compound

Participants

Reaction Steps

A mixture of 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid Compound 1c (1.0 g, 4.13 mmol) and 3-(tert-butyl-dimethyl-silanyloxymethyl)-benzene-1,2-diamine Compound 6a (1.05 g, 4.17 mmol), HATU (1.58 g, 4.16 mmol) and DIPEA (2.5 mL, 35.9 mmol) in DMF (50 mL) was stirred at room temperature overnight. The solvent was removed and the residue was dissolved in ethyl acetate (100 mL), then sequentially washed with hydrochloric acid (20 mL, 1M), water (30 mL×3) and brine (20 mL). The organic solution was evaporated to dryness in vacuo and purified by silica gel chromatography (10% to 50% of ethyl acetate in hexanes) to yield 5-bromo-1H-pyrazolo[3,4-b]pyridine-3-carboxylic acid [2-amino-3-(tert-butyl-dimethyl-silanyloxymethyl)-phenyl]-amide Compound 6b (1.21 g, 61% yield) as a yellow powder. 1H NMR (300 MHz, CDCl3) δ 8.91 (d, 1H, J=2.1 Hz), 8.73 (s, 1H), 8.67 (d, 1H, J=2.1 Hz), 7.47 (d, 1H, J=7.2 Hz), 7.01 (d, 1H, J=7.2 Hz), 6.83 (t, 1H, J=7.2 Hz), 4.78 (s, 2H), 0.95 (s; 9H), 0.11 (s, 6H); MS (ESI) m/z: 477 (M+H+).

Provenance & Evidence