Benzenesulfonyl chloride → HCID 68464675, compound

Participants

Reaction Conditions

Reaction Steps

To a stirred solution of Example 8 (150 mg, 0.487 mmol) in THF (15 mL) was added potassium t-butoxide (81 mg, 0.720 mmol) and 18-crown-6 (2 mg) at 0° C. The suspension was stirred for 10-15 min at 0° C. and then benzenesulfonyl chlorde (0.86 mg, 0.486 mmol) was added. The reaction mixture was further stirred at 0° C. for 30 min. and then stirred at room temperature for 3 hours. The reaction mixture was diluted with EtOAc and water. The organic layer was washed with saturated sodium bicarbonate, dried over sodium sulfate and concentrated under vacuum. The crude product was purified by column chromatography using EtOAc in hexanes (50%) to obtain methyl 2-[9-(phenylsulfonyl)-1,3,4,9-tetrahydro-2H-b-carbolin-2-yl]pyrimidine-5-carboxylate (60 mg). 1HNMR (200 MHz, DMSO-d6) ppm: 8.8 (s, 2H), 8.14-7.25 (m, 9H), 5.42 (s, 2H), 4.26 (t, 2H, J=5.4 Hz), 3.91 (s, 3H), 2.81 (2H, t, J=5.4 Hz); m/e=449 (M+1).

Provenance & Evidence