Methyl iodide → HCID 67209535, compound

Participants

Reaction Steps

N-(1-(1H-pyrrolo[2,3-b]pyridin-5-yl)ethyl)-2-(3-cyclopropyl-1,4-dimethyl-1H-pyrazolo[3,4-b]pyridin-6-yloxy)acetamide (example 6.57, 25 mg, 0.062 mmol) was dissolved in DMF (1 ml) and methyliodide (4.25 μl, 0.068 mmol) was added, followed by NaH (60% in mineral oil, 2.7 mg, 0.068 mmol). After stirring for 1 h at rt the reaction was diluted with EtOAc (1 ml) and water (2 ml) and extracted with EtOAc. The combined organic layers were washed with brine, dried over sodium sulfate, and the solvents were evaporated under reduced pressure. The crude product was purified on preparative TLC (DCM/MeOH 95/5) to give the product as colorless solid (15 mg, 58%). [1H-NMR (DMSO-d6, 600 MHz) δ 8.58 (d, 1H), 8.23 (s, 1H), 7.83 (s, 1H), 7.48 (d, 1H), 6.47 (s, 1H, 6.30 (d, 1H, 5.13-5.09 (m, 1H), 4.81 (d, 1H), 4.76 (d, 1H), 3.78 (s, 3H), 3.63 (s, 3H), 2.65 (s, 3H), 2.27-2.22 (m, 1H), 3.06 (d, 3H), 0.93-0.84 (m, 4H); LCMS RtL=2.901 min; [M+H]+=419.2]

Provenance & Evidence