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

HRID 2077447Notes

Reaction equation

HRID 2077447 reaction equation
[CH3:1][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.[Br:14][C:15]1[CH:22]=[C:21](F)[CH:20]=[CH:19][C:16]=1[C:17]#[N:18].[H-].[Na+].O>CN(C)C=O>[Br:14][C:15]1[CH:22]=[C:21]([N:4]2[C:5]3[CH2:6][C:7]([CH3:13])([CH3:12])[CH2:8][C:9](=[O:11])[C:10]=3[C:2]([CH3:1])=[CH:3]2)[CH:20]=[CH:19][C:16]=1[C:17]#[N:18]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 1189392-Bromo-4-fluorobenzonitrileHCID 248207983,6,6-trimethyl-6,7-dihydro-1H-indol-4(5H)-one

Product 1

HCID 118539082-Bromo-4-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-indol-1-yl)-benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
55 °C

Procedure

The title compound of Example 1 (9.8 g, 55.3 mmol) and 2-bromo-4-fluorobenzonitrile (13.27 g, 66.4 mmol) were dissolved in anhydrous dimethylformamide (DMF, 300 mL). To this was added sodium hydride (95%, 2.79 g, 111 mmol) and the reaction was stirred at 55° C. for 1 hour. The reaction mixture was cooled to room temperature and water was added. A tan solid precipitated which was filtered, washed with water and ether and then dried in vacuo (16.5 g, 84%). LCMS m/z: (M+H)=358.1.

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. customA tan solid precipitated which
  3. filtrationwas filtered
  4. washwashed with water and ether
  5. customdried in vacuo (16.5 g, 84%)

Sources & evidence

ORD record
ord-efcbc1eb1a9a4ca2b568ecb4b00e9814
Source dataset
uspto-grants-2011_04
Patent number
US07928135B2

Reaction notes

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