Water → HCID 71209178, compound

Participants

Reaction Conditions

Reaction Steps

A solution of ethyl 1-(3,4-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridine-5-carboxylate (6.5 g, 11.40 mmol) in anhydrous DCM (110 mL) was cooled to −55° C. and then DIBAL-H (22.80 mL, 22.80 mmol) (1M/toluene) was added dropwise in ˜20 min and the mixture was allowed to warm to 0° C. in 1 h and kept at 0° C. for 1 h. More DIBAL-H (12 mL, 12 mmol) was added and stirring at 0° C. continued for 1 h. The mixture was cooled to 0° C. and water (1.4 mL) was added slowly followed by 15% NaOH/water (1.4 mL) and water (3.5 mL). The mixture was stirred at RT for 15 min then filtered through a path of celite washing with dichloromethane. The filtrate was concentrated and co-evaporated with MeCN, dried in vacuo to provide (1-(3,4-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)methanol (5.0 g, 9.66 mmol, 85% yield) as an orange solid. 1H NMR and LCMS are consistent with proposed structure. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 1.80 (br s, 1 H), 2.83 (s, 3 H), 5.02 (d, J=2.15 Hz, 2 H), 5.40 (s, 2 H), 6.35 (d, J=3.51 Hz, 1 H), 6.92-7.12 (m, 3 H), 7.13 (d, J=3.51 Hz, 1 H); LCMS (m/z) ES+=415 (M+1).

Provenance & Evidence