HCID 12415565, compound → HCID 77230811, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 2-bromo-6-chlorothieno[2,3-b]pyridine-5-carbaldehyde (2.4 g, 8.7 mmol) (Meth-Cohn, O. Narine B. Tetrahedron Lett., 1978, 2045) in THF (50 mL) at −20° C. was added methylmagnesiumchloride (3.04 mL of 3N in THF, 9.1 mmol) dropwise. The reaction was stirred at −20° C. for 45 minutes and then quenched with 25 mL NH4Cl (sat) and 25 mL of water. The reaction was diluted with ether and the layers were separated. The organic layer was washed with brine and concentrated. Purification by column chromatography afforded 1-(2-bromo-6-chlorothieno[2,3-b]pyridin-5-yl)ethanol. LC/MS (M+1, found=293.8). 1H NMR (400 MHz, CDCl3) δ 8.21 (s, 1H), 7.30 (s, 1H), 5.32 (qd, J=6.3, 2.7 Hz, 1H), 2.19 (br s, 1H), 1.55 (d, J=6.3 Hz, 3H) ppm.

Provenance & Evidence