Cesium fluoride → HCID 53356864, compound

HRID 877482Notes

Reaction equation

[Cl:1][C:2]1[C:14]([Cl:15])=[CH:13][C:12]([Cl:16])=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH2:7][C:8](=[O:17])[C:9]=1[NH:10]2.[C:18]([Si](C)(C)C)([F:21])([F:20])[F:19].[F-].[Cs+]>C1COCC1>[Cl:1][C:2]1[C:14]([Cl:15])=[CH:13][C:12]([Cl:16])=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH2:7][C:8]([C:18]([F:21])([F:20])[F:19])([OH:17])[C:9]=1[NH:10]2

Participants

Conditions

Temperature: 0 °C

Procedure

To a solution of 5,6,8-trichloro-2,3,4,9-tetrahydro-1H-carbazol-1-one (0.1 g, 0.3 mmol) in anhydrous THF (5 mL), cooled to 0° C., CF3TMS (0.5 mL) followed by CsF (0.026 g, 0.17 mmol) were added. The reaction mixture was stirred at 0° C. for 1 h, cooled to room temperature and stirred for an additional 16 h, quenched with saturated NH4Cl (20 mL) and extracted with EtOAc (3×10 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 (3:17) as eluant] to afford the title compound as a yellow solid (0.042 g, 32%). 1H NMR (500 MHz, DMSO-d6, δ in ppm) 11.42 (s, 1H), 7.52 (s, 1H), 6.69 (s, 1H), 3.02 (m, 2H), 2.21 (m, 1H), 1.96 (m, 3H).

Workup

additionwere added
temperaturecooled to room temperature
stirringstirred for an additional 16 h
customquenched with saturated NH4Cl (20 mL)
extractionextracted with EtOAc (3×10 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 (3:17) as eluant]

Sources & evidence

ORD record: ord-ae875621f03c4646900027848b7e38b9
Source dataset: uspto-grants-2015_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08987319B2

Reaction notes

Loading…