1,2-Dichloroethane → HCID 68109168, compound

Participants

Reaction Steps

To a solution of the product of Example 60, step E (15 mg, 0.05 mmol) in 1,2-dichloroethane (0.5 mL) was added formaldehyde (12 μL, 37% in water). The reaction mixture was stirred at ambient temperature for 10 min before sodium triacetoxyborohydride (61 mg, 0.29 mmol) was added. The reaction mixture was stirred for 15 h, quenched with saturated sodium bicarbonate solution and extracted with chloroform. The organic layer was dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was treated with 1.25 M HCl in methanol and the resulting solution concentrated in vacuo to afford 2-methyl-7-(phenylsulfonyl)-1,2,3,4-tetrahydrobenzofuro[3,2-c]pyridine hydrochloride (9.5 mg, 61%, AUC HPLC 95.7%) as a white solid: mp 242-245° C.; 1H NMR (CD3OD, 300 MHz) δ 8.21-8.13 (m, 1H), 7.98 (d, J=7.2 Hz, 2H), 7.87 (dd, J=8.3 Hz, 1.2 Hz, 1H), 7.71 (d, J=8.1 Hz, 1H), 7.63-7.54 (m, 3H), 4.74-4.30 (br s, 2H), 3.96-3.60 (br s, 2H), 3.30 (br s, 2H), 3.13 (s, 3H); ESI MS m/z 328 [M+H]+.

Provenance & Evidence