Hydrochloric Acid → HCID 71534518, compound

Participants

Reaction Conditions

Reaction Steps

An ice cold solution of methyl 2-(tert-butoxy)-2-(4-(4-chlorophenyl)-6-methyl-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetate (20 mg, 0.043 mmol) in Tetrahydrofuran (THF) (0.5 mL) was treated with NaH (9.93 mg, 0.248 mmol) and allowed to stir at 0° C. for 10 minutes. The mixture was then treated with 4-fluorobenzenesulfonyl chloride (39.4 mg, 0.199 mmol) in one portion. The mixture was stirred for 10 minutes, quenched with water and then extracted with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The resultant was dissolved in Tetrahydrofuran (THF) (0.500 mL), treated with 2M LiOH (0.4 mL, 0.800 mmol) (2 M) and then stirred at ambient temperature overnight. The mixture was cooled to 0° C., treated with HCl (1M) until pH<2 and then extracted with ethyl acetate. The combined extracts were washed with brine, dried over Na2SO4, filtered and concentrated. The residue was purified by reverse phase chromatography (10-90% MeCN/H2O-0.1% TFA, 12 min) to afford the title compound. 1H NMR (400 MHz, CHLOROFORM-d) ppm 8.16-8.29 (m, 2H) 7.81-7.92 (m, 1H) 7.51-7.58 (m, 1H) 7.45-7.51 (m, 2H) 7.28-7.35 (m, 1H) 7.17-7.25 (m, 2H) 6.09-6.18 (m, 1H) 5.21-5.32 (m, 1H) 3.54-3.65 (s, 3H) 0.99 (s, 9H); LCMS (m/z) ES+=547 (M+1).

Provenance & Evidence