Water → HCID 57537631, compound

Participants

Reaction Conditions

Reaction Steps

5-Bromo-4-iodo-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (1.00 g, 2.21 mmol) and bis(tri-t-butylphosphine)palladium(0) (56 mg, 0.110 mmol) were combined and dissolved in anhydrous tetrahydrofuran (20 mL) in an oven-dried round-bottom flask. Dimethylzinc (552 μL, 1.11 mmol, 2.0 M solution in tetrahydrofuran). The solution was allowed to stir at 23° C. for 1 hour. To the mixture was added water (50 mL) followed by ethyl acetate (50 mL). Layers were mixed well, and the organic layer was stirred over sodium sulfate, filtered and concentrated in vacuo. The crude product was purified by flash silica gel chromatography using a gradient of ethyl acetate in hexanes to afford 5-Bromo-4-methyl-1-(2-trimethylsilanyl-ethoxymethyl)-1H-pyrrolo[2,3-b]pyridine (307 mg, 0.899 mmol, 41%) as a brown oil. 1H-NMR [500 MHz, d6-DMSO]: 8.43 (s, 1H), 7.71 (d, 1H), 6.79 (d, 1H), 5.69 (s, 1H), 3.61 (t, 2H), 2.66 (s, 3H), 0.93 (t, 2H), 0.0 (s, 9H); MS [MH+] m/z: 341.1, 343.0

Provenance & Evidence