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

HRID 1713941Notes

Reaction equation

HRID 1713941 reaction equation
[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[NH:9][C:8]=2[CH:20]=[CH2:21])[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.[H-].[Na+].[CH3:24][N:25]([CH3:30])[C:26](=[O:29])[CH2:27]Cl>CN(C=O)C>[CH:1]1([C:7]2[C:15]3[C:10](=[CH:11][C:12]([C:16]([O:18][CH3:19])=[O:17])=[CH:13][CH:14]=3)[N:9]([CH2:27][C:26]([N:25]([CH3:30])[CH3:24])=[O:29])[C:8]=2[CH:20]=[CH2:21])[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 758862-chloro-N,N-dimethylacetamideHCID 68435704methyl 3-cyclohexyl-2-vinyl-1H-indole-6-carboxylate

Product 1

HCID 68437081methyl 3-cyclohexyl-1-[2-(dimethylamino)-2-oxoethyl]-2-vinyl-1H-indole-6-carboxylateYield 68%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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)+.

Workup

  1. customall volatiles were evaporated
  2. washThe solution was washed with 1N HCl (1×), brine (2×)
  3. dry with materialdried over Na2SO4
  4. customThe solvent was evaporated
  5. customthe residual material crystallised from DCM with PE

Sources & evidence

ORD record
ord-435af86ffec84560b7b4f3a0250b714a
Source dataset
uspto-grants-2010_09
Patent number
US07795250B2

Reaction notes

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