Cesium fluoride → HCID 117962557, compound

HRID 877469Notes

Reaction equation

HRID 877469 reaction equation
[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]2[C:3]=1[C:4]1[CH2:5][CH2:6][CH2:7][C:8](=[O:16])[C:9]=1[NH:10]2.[F-].[Cs+].[C:19]([Si](C)(C)C)([F:22])([F:21])[F:20]>C1COCC1>[Cl:1][C:2]1[CH:14]=[CH:13][C:12]([Cl:15])=[C:11]2[C:3]=1[C:4]1[CH:5]([C:19]([F:22])([F:21])[F:20])[CH2:6][CH2:7][CH:8]([OH:16])[C:9]=1[NH:10]2

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 67378017HCID 67378017, compound

Product 1

HCID 117962557HCID 117962557, compoundYield 100.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 5,8-dichloro-2,3,4,9-tetrahydro-1H-carbazol-1-one (0.1 g, 0.39 mmol) in anhydrous THF (8 mL) at 0° C., CsF (59 mg, 0.39 mmol) and CF3TMS (0.56 g, 3.93 mmol) were added. The reaction mixture was slowly warmed to room temperature and stirred for 18 h. After the volatiles were removed in vacuo, the residue was diluted with water and extracted with EtOAc (2×15 mL) to give the crude compound which was purified by silica gel chromatography [EtOAc-hexane (1:4) as eluant] to give the title compound (0.127 g, 16%). 1H NMR (500 MHz, DMSO-d6, δ in ppm) 11.07 (s, 1H), 7.21 (d, J=8.0 Hz, 1H), 7.06 (d, J=8.5 Hz, 1H), 6.62 (s, 1H), 3.01-3.0 (m, 2H), 2.22-2.19 (m, 1H), 1.97-1.92 (m, 3H).

Workup

  1. customAfter the volatiles were removed in vacuo
  2. additionthe residue was diluted with water
  3. extractionextracted with EtOAc (2×15 mL)
  4. customto give the crude compound which
  5. customwas purified by silica gel chromatography [EtOAc-hexane (1:4) as eluant]

Sources & evidence

ORD record
ord-d78c424ef055410097446a464fb2d310
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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