Ammonium Hydroxide → 4-(trifluoromethyl)-1H-indole-5-carbonitrile

An NMP solution (15 mL) of N-{4-chloro-3-(trifluoromethyl)-2-[(trimethylsilyl)ethynyl]phenyl}-2,2-dimethylpropanamide (1.04 g, 2.77 mmol) was treated with CuCN (1.04 g, 11.01 mmol) and the resulting mixture was heated at 250° C. in a microwave for 5.5 h. The dark brown reaction mixture was poured into crushed ice (250 mL) containing conc. ammonium hydroxide (30 mL). The resulting slurry was filtered and rinsed with Et2O. The filtrate was diluted with Et2O (50 mL) and partitioned. The aqueous portion was extracted with Et2O (2×25 mL). The combined organic portions were washed with H2O (25 mL) and brine (25 mL). Drying (Na2SO4) and filtration were followed by concentration to a brown/yellow solid (0.723 g) that was used for the next reaction without further purification.

1. additionThe dark brown reaction mixture was poured
2. filtrationThe resulting slurry was filtered
3. washrinsed with Et2O
4. additionThe filtrate was diluted with Et2O (50 mL)
5. custompartitioned
6. extractionThe aqueous portion was extracted with Et2O (2×25 mL)
7. washThe combined organic portions were washed with H2O (25 mL) and brine (25 mL)
8. customDrying
9. filtration(Na2SO4) and filtration
10. concentrationwere followed by concentration to a brown/yellow solid (0.723 g) that
11. customwas used for the next reaction without further purification

ORD record

ord-15825b1769c84cbfbfcc6c2491abd412

Source dataset

uspto-grants-2014_03

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US08673948B2