Cesium fluoride → HCID 117962557, 화합물

HRID 877469노트

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HRID 877469 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 117962557HCID 117962557, 화합물수율 100.5%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

  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]

출처 및 근거

ORD 기록
ord-d78c424ef055410097446a464fb2d310
출처 데이터셋
uspto-grants-2015_03
특허 번호
US08987319B2

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