Methyl iodide → ethyl 1-methyl-5-nitro-3-phenyl-1H-indole-2-carboxylate

HRID 2118118Notes

Reaction equation

HRID 2118118 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[C:7]2[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)([O-:3])=[O:2].IC.[C:26]([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[CH3:26][N:9]1[C:10]2[C:6](=[CH:5][C:4]([N+:1]([O-:3])=[O:2])=[CH:12][CH:11]=2)[C:7]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[C:8]1[C:13]([O:15][CH2:16][CH3:17])=[O:14]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 10796Cesium carbonateHCID 741309ethyl 5-nitro-3-phenyl-1H-indole-2-carboxylate

Product 1

HCID 69231753ethyl 1-methyl-5-nitro-3-phenyl-1H-indole-2-carboxylateYield 105%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of ethyl 5-nitro-3-phenyl-1H-indole-2-carboxylate (1.0 g, 3.23 mmol) and iodomethane (2.5 mL, 40.2 mmol) in DMF (25 mL) was treated with Cs2CO3 (3.26 g, 10 mmol) and stirred for 16 h. The reaction was quenched by addition of water and the solid was collected and dried to yield ethyl 1-methyl-5-nitro-3-phenyl-1H-indole-2-carboxylate as a yellowish solid (1.1 g, 100%): 1H NMR (DMSO-d6) δ 1.03 (t, J=7.0 Hz, 3H, 4.09 (s, 3H, 4.18 (q, J=7.0 Hz, 2H, 7.40-7.55 (m, 5H, 7.90 (d, J=9.2 Hz, 1H, 8.23 (dd, J=9.2, 2.3 Hz, 1H, 8.32 (d, J=2.3 Hz, 1H; MS (EI) m/z 325.2 (MH+).

Workup

  1. customThe reaction was quenched by addition of water
  2. customthe solid was collected
  3. customdried

Sources & evidence

ORD record
ord-a42accc70b634a13bdf0929eeea1041d
Source dataset
uspto-grants-2008_10
Patent number
US07442805B2

Reaction notes

Loading…