Chloroform → 3-Piperidin-1-yl-1-triisopropylsilanyl-1H-indole

Participants

Reaction Conditions

Reaction Steps

Dissolve piperidine (1.28 mL, 12.9 mmol) in THF (10 mL) and treat with lithium bis(trimethylsilyl)-amide (1.0M in THF, 11.2 mL, 11.2 mmol). To the above solution add 3-bromo-1-triisopropylsilanyl-1H-indole (TCI-US, 3.04 g, 8.62 mmol), (2′-dicyclohexyl-phosphanyl-biphenyl-2-yl)-dimethyl-amine (88 mg, 0.22 mmol), and Pd2 dba3.CHCl3 (225 mg, 0.22 mmol). Heat the red solution to 70° C. for 4 h then cool to RT and concentrate. Purify the crude material by flash chromatography, using a linear gradient of 100% hexanes to 40% EtOAc/hexanes, to give the title compound (837 mg, 27%). MS (ES+) 357.2 (M+1)+. 1H NMR (400 MHz, CDCl3): δ 7.61 (d, 1H, J=8.4), 7.41 (d, 1H, J=8.4), 7.07 (m, 2H), 6.68 (s, 1H), 3.03 (m, 4H), 1.79 (m, 4H), 1.65 (septet, 3H, J=7.7), 1.58 (m, 2H), 1.12 (d, 18H, J=7.1).

Provenance & Evidence