N-bromobutanimide → Ethyl 3-Bromoindole-2-carboxylate

HRID 916188Notes

Reaction equation

HRID 916188 reaction equation
[Br:1]N1C(=O)CCC1=O.[NH:9]1[C:17]2[C:12](=[CH:13][CH:14]=[CH:15][CH:16]=2)[CH:11]=[C:10]1[C:18]([O:20][CH2:21][CH3:22])=[O:19]>CN(C=O)C>[CH2:21]([O:20][C:18]([C:10]1[NH:9][C:17]2[C:12]([C:11]=1[Br:1])=[CH:13][CH:14]=[CH:15][CH:16]=2)=[O:19])[CH3:22]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 73125Ethyl indole-2-carboxylate

Product 1

HCID 4715017Ethyl 3-Bromoindole-2-carboxylateYield 94.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A solution of N-bromosuccinimide (4.94 g, 27.7 mmol) in DMF (20 mL) was added dropwise to a stirred solution of ethyl 1H-indole-2-carboxylate (5.0 g, 26.4 mmol) in DMF (15 mL) at 0˜5° C. After the addition was completed, the reaction was warmed to room temperature and stirring was continued for an additional 1.5 h. The reaction mixture was poured over ice water and the resulting precipitate was collected and dried to give 3-bromo-1H-indolecarboxylic acid ethyl ester (6.68 g, 81%) as a white solid: 1H NMR (DMSO-d6) δ 1.37 (t, J=7.2 Hz, 3H), 4.38 (q, J=7.2 Hz, 2H), 7.18-7.22 (m, 1H), 7.34-7.38 (m, 1H), 7.50 (dd, J=8.3, 0.8 Hz, 1H), 7.55 (dd, J=8.3, 0.8 Hz, 1H), 12.22 (br s, 1H); MS (ESI) m/z 268 (MH+); 266 ([M−H]−).

Workup

  1. additionAfter the addition
  2. customthe resulting precipitate was collected
  3. customdried

Sources & evidence

ORD record
ord-588f401c690f4c33908754854d5a9666
Source dataset
uspto-grants-2007_09
Patent number
US07268159B2

Reaction notes

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