Isopropanol → HCID 68762560, compound

Participants

Reaction Conditions

Reaction Steps

To a solution of 1-bromo-3-fluorobenzene (0.066 ml, 0.59 mmol) in THF (0.3 mL) was added dropwise n-BuLi in hexane (0.23 ml, 0.52 mmol) at about −78° C. under nitrogen. After being stirred at about −78° C. for about 20 minutes, a solution of (R)-tert-butyl 5-(methoxy(methyl)carbamoyl)-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (0.050 g, 0.099 mmol) in THF (0.2 mL) was added dropwise to the reaction mixture at about −78° C. After 2 hours, i-PrOH (0.090 ml, 1.2 mmol) and water (2.0 mL) were added to the mixture, and the cold bath was removed. The mixture was stirred at about room temperature for about 20 minutes. The mixture was extracted with EtOAc. The combined organic layers were washed with water and brine, dried over MgSO4, and concentrated. The crude residue was purified by column chromatography (1-3% MeOH/DCM) to yield (R)-tert-butyl 5-(3-fluorobenzoyl)-1-(5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-1′-carboxylate (0.023 g, 43%). LCMS (APCI+) m/z 543.3 [M+H]+; Rt=4.49 min.

Provenance & Evidence