Potassium bis(trimethylsilyl)amide → HCID 86574196, compound

Participants

Reaction Conditions

Reaction Steps

An ice cold solution of 2-(1-benzyl-6-methyl-4-(5-methylchroman-6-yl)-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)-2-(tert-butoxy)acetic acid (210 mg, 0.408 mmol) in Tetrahydrofuran (THF) (3 mL) was treated with KHMDS (8.16 mL, 4.08 mmol) and then heated to 50° C. for 2 hours. Additional KHMDS (8.16 mL, 4.08 mmol) was added and the mixture was stirred at 70° C. overnight. The mixture was quenched with HCl (1M) at 0° C. and 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 2-(tert-butoxy)-2-(6-methyl-4-(5-methylchroman-6-yl)-7-oxo-6,7-dihydro-1H-pyrrolo[2,3-c]pyridin-5-yl)acetic acid (163 mg, 0.384 mmol, 94% yield) as white solid. 1H NMR (400 MHz, CHLOROFORM-d) ppm 11.20-11.38 (m, 1H) 7.28-7.40 (m, 1H) 6.93-7.05 (m, 1H) 6.70-6.82 (m, 1H) 5.84-6.01 (m, 1H) 5.25-5.57 (m, 1H) 4.15-4.28 (m, 2H) 3.74-3.90 (m, 3H) 2.61-2.78 (m, 2H) 2.04-2.19 (m, 2H) 1.87-2.06 (m, 2H) 0.94-1.26 (m, 9H); LCMS (m/z) ES+=425 (M+1).

Provenance & Evidence