Sodium hydride → methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-vinyl-1H-indole-6-carboxylate

関与物質

反応手順

To a solution of methyl 3-cyclohexyl-2-vinyl-1H-indole-6-carboxylate (from Step 1) in DMF, NaH (1.2 eq.; 60% in mineral oil) was added. After evolution of gas had ceased, N,N-dimethyl chloroacetamide (1.3 eq.) was added dropwise. The mixture was stirred overnight, then all volatiles were evaporated and the residual material was taken up in DCM. The solution was washed with 1N HCl (1×), brine (2×) and then dried over Na2SO4. The solvent was evaporated and the residual material crystallised from DCM with PE. The product was obtained as a yellow solid (68%). 1H NMR (400 MHz, DMSO-d6, 300 K) δ 1.36-1.38 (m, 3H); 1.69-1.96 (3m, 7H); 2.85 (s, 3H); 2.91-2.95 (m, 1H); 3.13 (s, 3H); 3.85 (s, 3H); 5.15 (s, 2H); 5.41 (d, J 17.8, 1H); 5.61 (d, J 11.6, 1H); 6.71-6.78 (dd, Ja 11.6, Jb 17.8, 1H); 7.61 (d, J 78.3, 1H); 7.81 (d, J 8.5, 1H); 7.94 (s, 1H). MS (ES+) m/z 369.6 (M+H)+.

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