Ethanol → HCID 53356846, compound

HRID 877471Notes

Reaction equation

[Cl:1][C:2]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH2:7][C:8]([C:31]([F:34])([F:33])[F:32])([O:26][Si](C)(C)C)[C:9]=1[N:10]2S(C1C=CC(C)=CC=1)(=O)=O.[OH-].[K+].CCO>C1COCC1.O>[Cl:1][C:2]1[C:14]([F:15])=[CH:13][CH:12]=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH2:7][C:8]([C:31]([F:32])([F:33])[F:34])([OH:26])[C:9]=1[NH:10]2

Participants

Conditions

Temperature: 60 °C

Procedure

To a solution of 5-chloro-6-fluoro-9-tosyl-1-(trifluoromethyl)-1-(trimethylsilyloxy)-2,3,4,9-tetrahydro-1H-carbazole (0.08 g, 0.15 mmol) in THF (5 mL), cooled to 0° C., KOH (0.042 g, 0.7 mmol) in H2O (1 mL) was added and the resulting mixture was stirred for 30 min. EtOH (4 mL) was added to the reaction mixture and heated to 60° C. for 3 h, diluted with water (10 mL) and extracted with EtOAc (4×15 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to obtain the crude compound which was purified by column chromatography [EtOAc-hexane (3:17) as eluant] to give the title compound (0.025 g, 55%). 1H NMR (500 MHz, DMSO-d6, δ in ppm) 11.22 (s, 1H), 7.34 (dd, J=9.0, 4.5 Hz, 1H), 7.14 (t, J=9.0 Hz, 1H), 6.70 (s, 1H), 3.09 (t, J=11.0 Hz, 1H), 2.94-2.89 (m, 1H), 2.10 (t, 6.5 Hz, 1H), 2.00-1.92 (m, 3H).

Workup

extractionextracted with EtOAc (4×15 mL)
dry with materialThe combined organic extracts were dried over Na2SO4
concentrationconcentrated under reduced pressure
customto obtain the crude compound which
customwas purified by column chromatography [EtOAc-hexane (3:17) as eluant]

Sources & evidence

ORD record: ord-8a4b3ba7c1204211a5ffd7ee5c7ea9e4
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987319B2

Reaction notes

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