Cesium carbonate → (R)-tert-butyl 2-(1'-benzyl-1-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4'-piperidine]-4-yl)pyrrolidine-1-carboxylate

Participants

Reaction Conditions

Reaction Steps

A mixture of (R)-tert-butyl 2-(1′-benzylspiro[indoline-3,4′-piperidine]-4-yl)pyrrolidine-1-carboxylate (50 mg, 0.11 mmol), (R)-4-chloro-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidine (19 mg, 0.11 mmol), Cs2CO3 (40 mg, 0.12 mmol), Pd(OAc)2 (3.0 mg, 0.01 mmol), Xantphos (7.0 mg, 0.01 mmol) in toluene (5 mL) was degassed by a nitrogen balloon, and the mixture was heated to 90° C. for 12 hours. The reaction mixture was filtered by a pad of celite and eluted with EtOAc. The filtrate was concentrated, and the residue was purified by flash chromatography to afford the product (R)-tert-butyl 2-(1′-benzyl-1-((R)-5-methyl-6,7-dihydro-5H-cyclopenta[d]pyrimidin-4-yl)spiro[indoline-3,4′-piperidine]-4-yl)pyrrolidine-1-carboxylate (15 mg, 23%) as a solid. 1H NMR (CDCl3, 400 MHz) δ 8.68 (s, 1H), 7.20-7.40 (m, 5H), 7.09-7.12 (m, 1H), 6.84-6.90 (m, 1H), 6.70-6.74 (m, 1H), 5.25-5.32 (m, 1H), 4.10-4.20 (m, 1H), 3.80-3.90 (m, 1H), 3.70-3.80 (m, 1H), 3.50-3.60 (m, 2H), 3.30-3.40 (m, 1H), 2.95-3.00 (m, 2H), 2.85-2.95 (m, 2H), 2.20-2.60 (m, 4H), 1.95-2.05 (m, 2H), 1.80-1.95 (m, 2H), 1.60-1.80 (m, 4H), 1.30 (s, 4H), 1.20 (s, 5H), 0.80-0.90 (m, 3H). MS (APCI+) [M+H]+ 580.

Provenance & Evidence