Sodium Carbonate Monohydrate → HCID 71209350, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of methyl 2-(1-(3,4-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-oxoacetate (845 mg, 1.528 mmol) in anhydrous toluene (13 mL) under nitrogen atmosphere was added (R)-CBS (0.382 mL, 0.382 mmol) (1M/toluene) and the mixture was cooled to −35° C. (EtOH/dry ice); catecholborane (4.74 mL, 4.74 mmol) (1M/THF) was slowly added dropwise over 1 h 15 min and then allowed to warm to −10° C. in ˜30 min and stirred at this temperature for 1 h. 2M Na2CO3/water and EtOAc was added and the mixture was stirred at RT for 5 min., diluted with EtOAc and water. The organic phase was washed with 2M Na2CO3, 1M NaOH/water, saturated NH4Cl, brine, dried (Na2SO4), concentrated, and purified by column chromatography to provide (S)-methyl 2-(1-(3,4-difluorobenzyl)-4-iodo-6-methyl-1H-pyrrolo[2,3-b]pyridin-5-yl)-2-hydroxyacetate (663 mg, 1.334 mmol, 87% yield) as a yellowish foam. 1H NMR (400 MHz, CHLOROFORM-d) δ ppm 2.69 (s, 3 H), 3.46 (d, J=2.35 Hz, 1 H), 3.81 (s, 3 H), 5.40-5.62 (m, 2 H), 5.91 (d, J=2.15 Hz, 1 H), 6.41 (d, J=3.52 Hz, 1 H), 6.93-7.20 (m, 4 H); LCMS (m/z) ES+=473 (M+1). Chiral HPLC (Whelk 0 SS 4.6×250 mm column with 25% IPA in hexane. UV was monitored at 215, 254, and 280 nm.): 94% ee.

Provenance & Evidence