N-bromobutanimide → 3-broMo-1H-indole-6-carbonitrile

HRID 389510Notes

Reaction equation

HRID 389510 reaction equation
[NH:1]1[C:9]2[C:4](=[CH:5][CH:6]=[C:7]([C:10]#[N:11])[CH:8]=2)[CH:3]=[CH:2]1.C1C(=O)N([Br:19])C(=O)C1>C(Cl)Cl>[Br:19][C:3]1[C:4]2[C:9](=[CH:8][C:7]([C:10]#[N:11])=[CH:6][CH:5]=2)[NH:1][CH:2]=1

Participants

4

Reactant 2

HCID 67184N-bromobutanimideHCID 851461H-indole-6-carbonitrile

Product 1

HCID 178048073-broMo-1H-indole-6-carbonitrileYield 100.5%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of 1H-indole-6-carbonitrile (1.6 g, 11.25 mmol) in DCM (60 mL) was added NBS (2.0 g, 11.25 mmol) in portions over a period of 5 minutes. The resultant mixture was stirred for 1 h. The reaction mixture was quenched with saturated sodium thiosulfate solution (25 mL) and further diluted with DCM (60 mL). The organic layer was washed with water (2×25 mL) followed by brine solution and dried over anhydrous sodium sulfate, filtered and concentrated to afford 2.50 g (99%) of the title compound, 1H NMR (300 MHz, CDCl3): δ 7.43 (d, J=7.4 Hz, 1 H), 7.45 (s, 1 H), 7.67 (d, J=6.9 Hz, 1 H), 7.79 (s, 1 H), 8.67 (br. s., 1H).

Workup

  1. customThe reaction mixture was quenched with saturated sodium thiosulfate solution (25 mL)
  2. additionfurther diluted with DCM (60 mL)
  3. washThe organic layer was washed with water (2×25 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-8c09f51cc67442cd8aab2d39f942de65
Source dataset
uspto-grants-2013_02
Patent number
US08378104B2

Reaction notes

Loading…