Sodium Sulfite → HCID 53353202, compound

Participants

Reaction Conditions

Reaction Steps

To N-(1-ethyl-1H-pyrrolo[3,2-c]pyridin-6-yl)-3-methyl-4-(prop-1-en-2-yl)benzamide (100 mg, 0.31 mmol) and methanesulfonamide (30 mg, 0.31 mmol) were added t-BuOH (1.6 mL). The mixture was cooled in ice bath, and then water (1.6 mL) and AD-mix-beta (550 mg, 0.39 mmol) were added to give a bi-phase orange solution. The reaction was stirred at 0° C. with slow warming to room temperature overnight. The mixture was again cooled in ice bath the next day, and a total of 500 mg of AD-mix-beta was added. No further conversion was observed after 6 hours. To the reaction mixture cooled in ice bath was added 120 mg of sodium sulfite. After being stirred for 20 min, the mixture was charged with brine (5 ml) and the mixture was extracted with EtOAc (2×5 ml). Combined organic layers were washed once with 2N KOH (5 ml) and then once with brine (5 ml). The organic layers were dried over Na2SO4, filtered, and concentrated. 1H NMR (DMSO-d6) δ: 10.47 (br. s., 1H), 8.65 (br. s., 1H), 8.29 (br. s., 1H), 7.81 (d, J=8.3 Hz, 2H), 7.56 (d, J=8.1 Hz, 1H), 7.48 (d, J=3.3 Hz, 1H), 6.58 (d, J=3.0 Hz, 1H), 4.91 (s, 1H), 4.76 (br. s., 1H), 4.16-4.28 (m, 2H), 3.60 (br. s., 2H), 2.59 (s, 3H), 1.48 (s, 3H), 1.39 (t, J=7.2 Hz, 3H); ESI-MS: m/z 354 (M+H)+.

Provenance & Evidence