6-Bromo-8-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazol-1-one → 1-Oxo-8-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile

HRID 877509Notes

Reaction equation

Br[C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([C:15]([F:18])([F:17])[F:16])[CH:14]=1)[NH:11][C:10]1[C:9](=[O:19])[CH2:8][CH2:7][CH2:6][C:5]2=1.[C:20]([Cu])#[N:21]>CN1C(=O)CCC1.O>[O:19]=[C:9]1[C:10]2[NH:11][C:12]3[C:4](=[CH:3][C:2]([C:20]#[N:21])=[CH:14][C:13]=3[C:15]([F:18])([F:17])[F:16])[C:5]=2[CH2:6][CH2:7][CH2:8]1

Participants

Conditions

Temperature: 210 °C

Procedure

6-Bromo-8-(trifluoromethyl)-2,3,4,9-tetrahydro-1H-carbazol-1-one (600 mg, 1.8 mmol) and CuCN (480 mg, 5.4 mmol) were mixed together in NMP (6 mL) and stirred at 210° C. under N2 atmosphere for 15 h. The reaction mixture was cooled to room temperature, diluted with water (20 mL) and filtered through a pad of Celite®. The aqueous layer was extracted with EtOAc (3×50 mL). The combined organic extracts were dried over Na2SO4 and concentrated in vacuo to obtain the crude material which was purified by washing with 10% EtOAc-hexane to afford the title compound as a pale brown solid (400 mg, 80%). 1H NMR (200 MHz, CDCl3, δ in ppm) 9.26 (bs, 1H), 8.22 (s, 1H), 7.86-7.90 (m, 1H), 3.09 (t, J=12.0 Hz, 2H), 2.77-2.70 (m, 2H), 2.40-2.31 (m, 2H). IR cm−1 2240 (CN)

Workup

temperatureThe reaction mixture was cooled to room temperature
filtrationfiltered through a pad of Celite®
extractionThe aqueous layer was extracted with EtOAc (3×50 mL)
dry with materialThe combined organic extracts were dried over Na2SO4
concentrationconcentrated in vacuo
customto obtain the crude material which
customwas purified
washby washing with 10% EtOAc-hexane

Sources & evidence

ORD record: ord-6703566469c14f94ac9a13426845f1bf
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987319B2

Reaction notes

Loading…