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

Temperature

250 °C

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-fe793d246e1e44a0879c58031c4d880a

Source dataset

uspto-grants-2009_08

DOI

10.6084/m9.figshare.5104873.v1

Patent number

US07572820B2