N-methyl-3-vinyl-1H-indole-2-carboxamide → 3-ethyl-N-methyl-1H-indole-2-carboxamide

HRID 1362433Notes

Reaction equation

HRID 1362433 reaction equation
[CH3:1][NH:2][C:3]([C:5]1[NH:6][C:7]2[C:12]([C:13]=1[CH:14]=[CH2:15])=[CH:11][CH:10]=[CH:9][CH:8]=2)=[O:4]>C(OCC)(=O)C.[Pd]>[CH2:14]([C:13]1[C:12]2[C:7](=[CH:8][CH:9]=[CH:10][CH:11]=2)[NH:6][C:5]=1[C:3]([NH:2][CH3:1])=[O:4])[CH3:15]

Participants

4

Reactant 1

HCID 59277607N-methyl-3-vinyl-1H-indole-2-carboxamide

Product 1

HCID 592775313-ethyl-N-methyl-1H-indole-2-carboxamideYield 90%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of N-methyl-3-vinyl-1H-indole-2-carboxamide (1.1 g, 5.4 mmol) and 10% Pd/C (55 mg) in ethyl acetate (150 mL) was stirred for 3 h under an atmosphere of hydrogen. The mixture was filtered through celite and evaporated to afford the title compound (970 mg 90%). 1H NMR (400 MHz, DMSO-d6) δ 11.05 (s, 1H), 7.80 (s, 1H), 7.59 (d, J=7.6 Hz, 1H), 7.36 (d, J=8.4 Hz, 1H), 7.17 (t, J=6.8 Hz, 1H), 7.04 (t, J=6.0 Hz, 1H), 3.01 (q, J=7.4 Hz, 2H), 2.81 (d, J=4.6 Hz, 3H), 1.17 (t, J=7.4 Hz, 3H).

Workup

  1. filtrationThe mixture was filtered through celite
  2. customevaporated

Sources & evidence

ORD record
ord-35279fd4df564a9f975ee033b0444883
Source dataset
uspto-grants-2011_02
Patent number
US07879872B2

Reaction notes

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