Stannane, tributyl(phenylmethyl)- → 6,6-Dimethyl-3-phenylmethyl-1-(pyridin-2-yl)-4,5,6,7-tetrahydroindol-4-one

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Reaction Steps

A solution of 3-bromo-6,6-dimethyl-1-(pyridin-2-yl)-4,5,6,7-tetrahydroindol-4-one (10 mg, 0.31 mmol), benzyltributylstannane (253 mg, 0.68 mmol) and dichlorobis(triphenylphosphine)palladium (50 mg, 0.08 mmol) in hexamethylphosphoramide (1 mL) was heated at 70° C. for 48 h. The mixture was cooled to room temperature, diluted with DCM (2 mL), and the solution chromatographed on silica gel, eluting with isohexane: EtOAc (4:1). The title compound (45 mg, 43%) was isolated as a colourless solid. mp 111-113° C. Found: C, 79.7; H, 6.7; N, 8.3%. Calc. C22H22N2O: C, 79.97; H, 6.71; N, 8.48%. 1H NMR (360 MHz, CDCl3) δ 1.11 (6H,s), 2.39 (2H,s), 2.93 (2H,s), 4.17 (2H,s), 6.61 (1H,s), 7.16-7.34 (7H,m), 7.77 (1H, d of t, J=7.7 and 1.9 Hz), 8.50-8.53 (1H,m). MS (ES+) 331 (M+1).

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