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

Participants

Role	Name	HCID	Charge
Reactant	Water	HCID 962	—
Reactant	Sodium hydride	HCID 24758	—
Reactant	2-Bromo-4-fluorobenzonitrile	HCID 118939	—
Reactant	3,6,6-trimethyl-6,7-dihydro-1H-indol-4(5H)-one	HCID 24820798	—
Solvent	Dimethylformamide	HCID 6228	—
Product	2-Bromo-4-(3,6,6-trimethyl-4-oxo-4,5,6,7-tetrahydro-indol-1-yl)-benzonitrile	HCID 11853908	—

Reaction Conditions

Temperature	55 °C

Reaction Steps

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.

Provenance & Evidence

DOI	10.6084/m9.figshare.5104873.v1
Patent number	US07906529B2
Source dataset	uspto-grants-2011_03
ORD ID	ord-a3b86bb8ea884f77b52f54f5be1d2fda
Source note	uspto-grants-2011_03