Potassium Carbonate → Trans-2-(2-(Trifluoromethyl)Cyclopropyl)Naphthalene

HRID 1024551

반응식

HRID 1024551 반응식
C1C2C(=CC=CC=2)C=CC=1OS([C:15]([F:18])([F:17])[F:16])(=O)=O.C1(P(C2CCCCC2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][C:27]=2[C:32]2[C:37](OC(C)C)=[CH:36][CH:35]=[CH:34][C:33]=2OC(C)C)CCCCC1.[C:52]([O-])([O-])=O.[K+].[K+]>C1(C)C=CC=CC=1.O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:16][C:15]([F:18])([F:17])[C@@H:26]1[CH2:31][C@H:30]1[C:29]1[CH:28]=[CH:27][C:32]2[C:33](=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:52]=1

참가 물질

7

반응물 3

HCID 11430Potassium CarbonateHCID 45463412-Naphthyl TrifluoromethanesulfonateHCID 162179852-Dicyclohexylphosphino-2',6'-diisopropoxybiphenyl

생성물 1

HCID 67775384Trans-2-(2-(Trifluoromethyl)Cyclopropyl)Naphthalene수율 388.6%

시약·촉매·용매 3

HCID 167845palladium(II) acetate촉매HCID 962Water용매HCID 1140Toluene용매

반응 조건

온도
100 °C

실험 절차

In an open vial with pressure-release top, a stirred mixture of 2-naphthyltrifluoromethanesulfonate (Aldrich, St. Louis, Mo.) (69 mg, 0.25 mmol), palladium(II) acetate (5.5 mg, 0.025 mmol), 2-dicyclohexylphosphino-2′,6′-diisopropoxybiphenyl (23 mg, 0.05 mmol), K2CO3 (138 mg, 1.0 mmol) and trans-2-(trifluoromethyl)cyclopropylboronic acid MIDA ester (99 mg, 0.38 mmol) in toluene (2.5 mL) and H2O (0.5 mL) was de-gassed with N2 for 15 minutes, then the reaction mixture placed under nitrogen, sealed and heated to 100° C. and stirred for 6 hours. After allowing to cool, the reaction mixture was diluted with H2O (15 mL) and EtOAc (20 mL), filtered through Celite and the filter cake washed with EtOAc (2×20 mL). The filtrate was partitioned and the aqueous layer extracted with EtOAc (2×15 mL). The combined organic extracts were dried (Na2SO4), filtered and concentrated under vacuum to leave a crude residue. The residue was purified by preparative thin-layer chromatography (2 prep TLC plates used) using EtOAc/hexane (1:99) as eluent to give the product (45.9 mg, 78%) as a solid.

후처리

  1. customwas de-gassed with N2 for 15 minutes
  2. customsealed
  3. temperatureto cool
  4. additionthe reaction mixture was diluted with H2O (15 mL) and EtOAc (20 mL)
  5. filtrationfiltered through Celite
  6. washthe filter cake washed with EtOAc (2×20 mL)
  7. customThe filtrate was partitioned
  8. extractionthe aqueous layer extracted with EtOAc (2×15 mL)
  9. dry with materialThe combined organic extracts were dried (Na2SO4)
  10. filtrationfiltered
  11. concentrationconcentrated under vacuum
  12. customto leave a crude residue
  13. customThe residue was purified by preparative thin-layer chromatography (2 prep TLC plates used)

출처 및 근거

ORD 기록
ord-bdb790f423af44db82e29322d576eeeb
출처 데이터셋
uspto-grants-2014_05
특허 번호
US08722916B2

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