Water → 2-(3-Bromo-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-1H-indol-1-yl)benzonitrile

HRID 1937637Notes

Reaction equation

HRID 1937637 reaction equation
[Br:1][C:2]1[C:10]2[C:9](=[O:11])[CH2:8][C:7]([CH3:13])([CH3:12])[CH2:6][C:5]=2[NH:4][CH:3]=1.F[C:15]1[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=1[C:17]#[N:18].C([O-])([O-])=O.[K+].[K+].O>CS(C)=O>[Br:1][C:2]1[C:10]2[C:9](=[O:11])[CH2:8][C:7]([CH3:13])([CH3:12])[CH2:6][C:5]=2[N:4]([C:15]2[CH:22]=[CH:21][CH:20]=[CH:19][C:16]=2[C:17]#[N:18])[CH:3]=1

Participants

6

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 678552-FluorobenzonitrileHCID 22461280HCID 22461280, compound

Product 1

HCID 224613032-(3-Bromo-4,5,6,7-tetrahydro-6,6-dimethyl-4-oxo-1H-indol-1-yl)benzonitrileYield 91%

Reagents, catalysts & solvents 1

HCID 679Dimethyl SulfoxideSolvent

Procedure

A solution of 3-bromo-6,6-dimethyl-4,5,6,7-tetrahydro-1H-indol-4-one (670 mg, 2.77 mmol), 2-fluorobenzonitrile (0.3 mL, 2.77mmol) and K2CO3 (957 mg, 6.9 mmol) in DMSO (10 mL) was stirred at 100° C. for 3 h. The mixture was cooled to room temperature, poured into water and extracted into EtOAc (3×). The combined organic layers were washed with water (2×), dried (MgSO4) and evaporated. The title compound (858 mg, 91%) was isolated as a beige solid and used without further purification. 1H NMR (400 MHz, CDCl3) δ 1.10 (6H,s), 2.42 (2H,s), 2.51 (2H,s), 6.83 (1H,s), 7.42 (1H,dd, J=7.9 and 0.9Hz), 7.64 (1H,dd, J=7.7 and 1.1 Hz), 7.78 (1H,dd, J=7.9 and 1.5 Hz), 7.85 (1H,dd, J=7.7 and 1.4 Hz). MS (ES+) 343/345 (M+1).

Workup

  1. extractionextracted into EtOAc (3×)
  2. washThe combined organic layers were washed with water (2×)
  3. dry with materialdried (MgSO4)
  4. customevaporated

Sources & evidence

ORD record
ord-a3c72ecaa57f4e1088cbf2ec5d127b6e
Source dataset
uspto-grants-2002_05
Patent number
US06395766B1

Reaction notes

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