N-bromobutanimide → tert-butyl 5-(bromomethyl)-2-cyano-1H-indole-1-carboxylate

HRID 1505654Notes

Reaction equation

HRID 1505654 reaction equation
[C:1]([C:3]1[N:4]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH3:12])=[CH:7][CH:6]=2)#[N:2].[Br:20]N1C(=O)CCC1=O>C(Cl)(Cl)(Cl)Cl.CC(N=NC(C#N)(C)C)(C#N)C>[C:1]([C:3]1[N:4]([C:13]([O:15][C:16]([CH3:19])([CH3:18])[CH3:17])=[O:14])[C:5]2[C:10]([CH:11]=1)=[CH:9][C:8]([CH2:12][Br:20])=[CH:7][CH:6]=2)#[N:2]

Participants

5

Reactant 2

HCID 67184N-bromobutanimideHCID 90405540tert-butyl 2-cyano-5-methyl-1H-indole-1-carboxylate

Product 1

HCID 90404208tert-butyl 5-(bromomethyl)-2-cyano-1H-indole-1-carboxylateYield 78%

Reagents, catalysts & solvents 2

HCID 6547AzobisisobutyronitrileCatalystHCID 5943Carbon TetrachlorideSolvent

Procedure

To a stirred solution of 334 mg of tert-butyl 2-cyano-5-methyl-1H-indole-1-carboxylate (1.3 mmol) in carbon tetrachloride (5 mL) was added 232 mg of N-bromosuccinimide (1.3 mmol) and 11 mg of AIBN (0.065 mmol). The mixture was refluxed for 1 h, then cooled and concentrated, and the residues were purified by chromatography on silica gel using hexane-ethyl acetate 20:1 to give 340 mg of tert-butyl 2-cyano-5-bromomethyl-1H-indole-1-carboxylate. 1H NMR (600 MHz, CDCl3): δ 8.22 (d, 1H, J=8.8 Hz), 7.64 (s, 1H), 7.53 (d, 1H, J=8.8 Hz), 7.31 (s, 1H), 4.60 (s, 2H), 1.73, (s, 9H). 13C NMR (150 MHz, CDCl3): δC 147.64, 136.27, 133.92, 129.34, 127.45, 122.33, 121.15, 116.46, 113.02, 109.75, 87.14, 33.23, 28.01.

Workup

  1. temperatureThe mixture was refluxed for 1 h
  2. temperaturecooled
  3. concentrationconcentrated
  4. customthe residues were purified by chromatography on silica gel

Sources & evidence

ORD record
ord-051e2641f8a3463cae9c3bd919ce5038
Source dataset
uspto-grants-2015_12
Patent number
US09216993B2

Reaction notes

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