4-bromo-5-fluoro-2,3-dihydro-1H-inden-1-one → 5-fluoro-1-oxo-2,3-dihydro-1H-indene-4-carbonitrile
Reaction equation
Br[C:2]1[C:10]([F:11])=[CH:9][CH:8]=[C:7]2[C:3]=1[CH2:4][CH2:5][C:6]2=[O:12].[Cu][C:14]#[N:15]>CN(C=O)C>[F:11][C:10]1[CH:9]=[CH:8][C:7]2[C:6](=[O:12])[CH2:5][CH2:4][C:3]=2[C:2]=1[C:14]#[N:15]Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 150 °C
Procedure
To a flask charged with 4-Bromo-5-fluoro-2,3-dihydro-1H-inden-1-one [made following the procedure described in Intermediate 35, Step B of PCT publication WO 2010/129379) (1.0 g, 4.4 mmol) and a stir bar was added copper(I) cyanide (0.47 g, 5.2 mmol) and DMF (20 ml). The reaction was sealed with a condenser, purged three times with nitrogen, and heated to 150° C. for 16 hours. TLC at that point showed two new spots. The spot right below SM was the title product. LC-MS (IE, m/z): 176 [M+1].