Potassium Carbonate → HCID 22461262, compound

Participants

Reaction Steps

A solution of 6,6-dimethyl-3-ethyl-4,5,6,7-tetrahydro-1H-indole-4-one (100 mg, 0.52 mmol), K2CO3 (87 mg, 0.63 mmol), copper (I) bromide (15 mg, 0.1 mmol) and 2-chloropyrimidine (71 mg, 0.63 mmol) in DMF (1 mL) were heated at 180° C. for 24 h. More copper (I) bromide (16 mg, 0.1 mmol) and 2-chloropyrimidine (50 mg) were added and heating continued for a further 24 h. The DMF was evaporated and the residue partitioned between water and DCM. The organic layer was separated and the aqueous phase extracted with DCM (2×). The combined organic layers were washed with water, dried (MgSO4) and evaporated. The residue was chromatographed on silica gel, eluting with 4:1 isohexane: EtOAc, to afford the title compound (35 mg, 25%) as a yellow solid. mp 111-114° C. Found: C, 71.07; H, 6.98; N, 15.20%. Calc C16H19N3O: C, 71.35; H, 7.11; N, 15.60%. 1H NMR (360 MHz, d6-DMSO) δ 1.06 (6H,s), 1.15 (3H,t, J=7.4 Hz), 2.30 (2H,s), 2.67 (2H,q, J=7.3 Hz), 3.23 (2H,s), 7.44 (1H,t, J=4.8Hz), 7.47 (1H,s), 8.86 (2H,d, J=4.8Hz). MS (ES+) 270 (+1).

Provenance & Evidence