N-bromobutanimide → Ethyl 3-bromo-5-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylate

HRID 1875038Notes

Reaction equation

HRID 1875038 reaction equation
[Br:1]N1C(=O)CCC1=O.[CH3:9][C:10]([O:13][C:14]([NH:16][C:17]1[CH:18]=[C:19]2[C:23](=[CH:24][CH:25]=1)[NH:22][C:21]([C:26]([O:28][CH2:29][CH3:30])=[O:27])=[CH:20]2)=[O:15])([CH3:12])[CH3:11]>ClCCl>[Br:1][C:20]1[C:19]2[C:23](=[CH:24][CH:25]=[C:17]([NH:16][C:14]([O:13][C:10]([CH3:9])([CH3:11])[CH3:12])=[O:15])[CH:18]=2)[NH:22][C:21]=1[C:26]([O:28][CH2:29][CH3:30])=[O:27]

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 22105416Ethyl 5-[(tert-butoxycarbonyl)amino]-1H-indole-2-carboxylate

Product 1

HCID 68484480Ethyl 3-bromo-5-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylateYield 90.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

N-Bromosuccinimide (0.095 g, 0.536 mmol) was added to a solution of ethyl 5-({[(1,1-dimethylethyl)oxy]carbonyl}amino)-1H-indole-2-carboxylate (0.163 g, 0.536 mmol) in dichloromethane (5 mL). The mixture was stirred at room temperature overnight. The solvent was evaporated. The residue was taken up in ethyl acetate and washed with water. The organic layer was dried over sodium sulfate and concentrated to give the title compound (0.186 g, 48%) as an off-white solid. 1H NMR (400 MHz, chloroform-d) δ ppm 8.97 (br. s., 1H), 7.70 (s, 1H), 7.28-7.39 (m, 2H), 6.54 (br. s., 1H), 4.33-4.54 (m, 2H), 1.54 (s, 9H), 1.39-1.48 (m, 3H). ES MS: m/z 381, 383.

Workup

  1. customThe solvent was evaporated
  2. washwashed with water
  3. dry with materialThe organic layer was dried over sodium sulfate
  4. concentrationconcentrated

Sources & evidence

ORD record
ord-7e37500eefd7420fb141a1286809050b
Source dataset
uspto-grants-2012_11
Patent number
US08304419B2

Reaction notes

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