Potassium Carbonate → Ethyl 1-[(4-nitrophenyl)methyl]-1H-indole-2-carboxylate

HRID 916179Notes

Reaction equation

HRID 916179 reaction equation
[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8]Br)=[CH:6][CH:5]=1)([O-:3])=[O:2].[CH2:12]([O:14][C:15]([C:17]1[NH:18][C:19]2[C:24]([CH:25]=1)=[CH:23][CH:22]=[CH:21][CH:20]=2)=[O:16])[CH3:13].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[N+:1]([C:4]1[CH:11]=[CH:10][C:7]([CH2:8][N:18]2[C:19]3[C:24](=[CH:23][CH:22]=[CH:21][CH:20]=3)[CH:25]=[C:17]2[C:15]([O:14][CH2:12][CH3:13])=[O:16])=[CH:6][CH:5]=1)([O-:3])=[O:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 660114-Nitrobenzyl bromideHCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 15090439Ethyl 1-[(4-nitrophenyl)methyl]-1H-indole-2-carboxylateYield 72%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of 4-nitrobenzyl bromide (1.85 g, 8.56 mmol), 1H-indole-2-carboxylic acid ethyl ester (1.62 g, 8.56 mmol) and potassium carbonate (4.17 g, 30 mmol) in 100 mL of acetone was refluxed for 1 day. After cooling to room temperature the reaction was quenched by addition of water and then partitioned between water and methylene chloride. The organic phase was dried over MgSO4, and concentrated to yield ethyl 1-(4-nitrobenzyl)-1H-indole-2-carboxylate as an off-white solid (2.0 g, 72%): 1H NMR (DMSO-d6) δ 1.27 (t, J=7.1 Hz, 3H), 4.26(q, J=7.1 Hz, 3H), 5.99(s, 2H), 7.18(t, J=7.0 Hz, 1H), 7.22 (d, J=9.0-Hz, 2H), 7.34 (t, J=7.0 Hz, 1H), 7.43 (s, 1H), 7.58 (d, J=13.8 Hz, 1H), 7.76 (d, J=13.8 Hz, 1H), 8.15 (d, J=9.0 Hz, 2H); MS (ESI) m/z 325 (MH+).

Workup

  1. temperaturewas refluxed for 1 day
  2. customwas quenched by addition of water
  3. custompartitioned between water and methylene chloride
  4. dry with materialThe organic phase was dried over MgSO4
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-ddbc141521a84329aaaa9fbcebaaa34b
Source dataset
uspto-grants-2007_09
Patent number
US07268159B2

Reaction notes

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