Cesium carbonate → 1-(1'-benzyl-1-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4'-piperidine]-4-yl)ethanol

Participants

Reaction Conditions

Reaction Steps

A flask was charged with Pd(OAc)2 (0.0027 g, 0.012 mmol) and Xantphos (0.010 g, 0.018 mmol) and purged with nitrogen. The flask was then charged with (R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine (0.022 g, 0.13 mmol), 1-(1′-benzylspiro[indoline-3,4′-piperidine]-4-yl)ethanol (0.047 g, 0.12 mmol), Cs2CO3 (0.058 g, 0.18 mmol), and toluene (0.6 mL) The reaction was purged with nitrogen and heated to 100° C. for 3 hours. Additional (R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine was added, and the reaction was heated at 100° C. for an additional 4 hours and then stirred at room temperature overnight. The reaction was filtered through GFF and concentrated under reduced pressure. The crude residue was purified by column chromatography (5% MeOH/DCM, then 5% 7N NH4 in MeOH/DCM) to yield 1-(1′-benzyl-1-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)ethanol (0.017 g, 31%). LCMS (APCI+) m/z 455.2 [M+H]+; Rt=3.18 min.

Provenance & Evidence