Potassium Hydroxide → HCID 52943808, compound

HRID 877459Notes

Reaction equation

S([N:11]1[C:23]2[C:22]([C:29]([F:32])([F:31])[F:30])([O:24][Si](C)(C)C)[CH2:21][CH2:20][CH2:19][C:18]=2[C:17]2[C:12]1=[CH:13][CH:14]=[C:15]([C:33]#[N:34])[CH:16]=2)(C1C=CC(C)=CC=1)(=O)=O.[OH-].[K+]>C1COCC1.O>[OH:24][C:22]1([C:29]([F:32])([F:30])[F:31])[C:23]2[NH:11][C:12]3[C:17](=[CH:16][C:15]([C:33]#[N:34])=[CH:14][CH:13]=3)[C:18]=2[CH2:19][CH2:20][CH2:21]1

Participants

Conditions

Temperature: 55 °C

Procedure

9-Tosyl-1-(trifluoromethyl)-1-(trimethylsilyloxy)-2,3,4,9-tetrahydro-1H-carbazole-6-carbonitrile (0.03 g, 0.06 mmol) was dissolved in THF (2 mL) and KOH (11 mg, 0.2 mmol), in H2O (2 mL) was added. The reaction mixture was heated to 55° C. for 24 h, then cooled to room temperature, diluted with water (5 mL) and extracted with EtOAc (3×5 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to give the crude compound which was purified by column chromatography [EtOAc-hexane (1:9) as eluant] to afford the title compound as a white solid (15 mg, 79%). 1H NMR (500 MHz, CDCl3, δ in ppm) 8.4 (bs, 1H), 7.9 (s, 1H), 7.49 (d, J=9.0 Hz, 1H), 7.44 (d, J=8.0 Hz, 1H), 2.89-2.85 (m, 1H), 2.76-2.74 (m, 1H), 2.45 (s, 1H), 2.32-2.28 (m, 1H), 2.14-2.12 (m, 2H), 2.05-2.03 (m, 1H).

Workup

temperaturecooled to room temperature
extractionextracted with EtOAc (3×5 mL)
dry with materialThe combined organic extracts were dried over Na2SO4
concentrationconcentrated under reduced pressure
customto give the crude compound which
customwas purified by column chromatography [EtOAc-hexane (1:9) as eluant]

Sources & evidence

ORD record: ord-b7ee30b7cd1240d18e3cdeedf967800c
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987319B2

Reaction notes

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