Cesium fluoride → HCID 53356882, compound

HRID 877503Notes

Reaction equation

HRID 877503 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([F:15])[CH:14]=1)[NH:11][C:10]1[C:9](=[O:16])[CH2:8][CH2:7][CH2:6][C:5]2=1.[C:17]([Si](C)(C)C)([F:20])([F:19])[F:18].[F-].[Cs+]>C1COCC1>[Cl:1][C:2]1[CH:3]=[C:4]2[C:12](=[C:13]([F:15])[CH:14]=1)[NH:11][C:10]1[C:9]([C:17]([F:20])([F:19])[F:18])([OH:16])[CH2:8][CH2:7][CH2:6][C:5]2=1

Participants

5

Reactant 3

HCID 25953Cesium fluorideHCID 552549(Trifluoromethyl)trimethylsilaneHCID 67377568HCID 67377568, compound

Product 1

HCID 53356882HCID 53356882, compoundYield 8.3%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
0 °C

Procedure

To a solution of 6-chloro-8-fluoro-2,3,4,9-tetrahydro-1H-carbazol-1-one (0.15 g, 0.63 mmol) in anhydrous THF (12 mL), cooled to 0° C., CF3TMS (1 mL, 6.3 mmol) followed by CsF (0.28 g, 1.8 mmol) were added. The reaction mixture was stirred at 0° C. for 6 h, quenched with saturated NH4Cl (10 mL) and extracted with EtOAc (2×15 mL). The combined organic extracts were dried over Na2SO4 and concentrated under reduced pressure to obtain the crude material which was purified by column chromatography [EtOAc-hexanes (3:22) as eluant] to give the title compound (0.016 g, 8%). 1H NMR (200 MHz, CDCl3, δ in ppm) 8.35 (bs, 1H), 7.30 (s, 1H), 7.00 (d, J=4.2 Hz, 1H), 2.82-2.79 (m, 1H), 2.70-2.68 (m, 1H), 2.47 (s, 1H), 2.28-2.24 (m, 1H), 2.12-2.10 (m, 2H), 2.03-2.02 (m, 1H).

Workup

  1. additionwere added
  2. customquenched with saturated NH4Cl (10 mL)
  3. extractionextracted with EtOAc (2×15 mL)
  4. dry with materialThe combined organic extracts were dried over Na2SO4
  5. concentrationconcentrated under reduced pressure
  6. customto obtain the crude material which
  7. customwas purified by column chromatography [EtOAc-hexanes (3:22) as eluant]

Sources & evidence

ORD record
ord-f5a76aecbea84414bd45eaff72f6711e
Source dataset
uspto-grants-2015_03
Patent number
US08987319B2

Reaction notes

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