Potassium Fluoride → 2'-fluoro-5'-methoxy-2-(2,2,6,6-tetramethyl-3,6-dihydro-2H-pyran-4-yl)biphenyl-4-ol

HRID 1049590

반응식

HRID 1049590 반응식
FC(F)(F)S(O[C:7]1[CH:12]=[C:11]([O:13][Si](C(C)(C)C)(C)C)[CH:10]=[CH:9][C:8]=1[C:21]1[CH:26]=[C:25]([O:27][CH3:28])[CH:24]=[CH:23][C:22]=1[F:29])(=O)=O.[CH3:32][C:33]1([CH3:50])[CH2:38][C:37](B2OC(C)(C)C(C)(C)O2)=[CH:36][C:35]([CH3:49])([CH3:48])[O:34]1.C1(P(C2CCCCC2)C2C=CC=CC=2C2C(C(C)C)=CC(C(C)C)=CC=2C(C)C)CCCCC1.[F-].[K+]>C(OCC)(=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1.CO>[F:29][C:22]1[CH:23]=[CH:24][C:25]([O:27][CH3:28])=[CH:26][C:21]=1[C:8]1[CH:9]=[CH:10][C:11]([OH:13])=[CH:12][C:7]=1[C:37]1[CH2:36][C:35]([CH3:49])([CH3:48])[O:34][C:33]([CH3:50])([CH3:32])[CH:38]=1

참가 물질

9

반응물 4

HCID 522689Potassium FluorideHCID 111557942-Dicyclohexylphosphino-2',4',6'-triisoprophylbiphenylHCID 467380002,2,6,6-Tetramethyl-3,6-dihydro-2H-pyran-4-boronic acid pinacol esterHCID 131736033HCID 131736033, 화합물

생성물 1

HCID 1177600932'-fluoro-5'-methoxy-2-(2,2,6,6-tetramethyl-3,6-dihydro-2H-pyran-4-yl)biphenyl-4-ol수율 41.6%

시약·촉매·용매 4

HCID 167845palladium(II) acetate촉매HCID 887Methanol용매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

반응 조건

온도
100 °C

실험 절차

To a mixture of 4-((tert-butyl(dimethyl)silyl)oxy)-2′-fluoro-5′-methoxybiphenyl-2-yl trifluoromethanesulfonate (405 mg), 2,2,6,6-tetramethyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-3,6-dihydro-2H-pyran (452 mg), palladium acetate (20 mg), dicyclohexyl(2′,4′,6′-triisopropylbiphenyl-2-yl)phosphine (83 mg), methanol (3 mL) and toluene (3 mL) was added potassium fluoride (151 mg) and, under microwave irradiation, the mixture was stirred at 100° C. for 20 min. The reaction mixture was diluted with ethyl acetate. The diluted solution was washed with water and saturated brine, and dried over anhydrous sodium sulfate. The solvent was evaporated under reduced pressure, and the residue was purified by silica gel column chromatography (ethyl acetate/hexane) to give the title compound (125 mg) as white crystals.

후처리

  1. customunder microwave irradiation
  2. washThe diluted solution was washed with water and saturated brine
  3. dry with materialdried over anhydrous sodium sulfate
  4. customThe solvent was evaporated under reduced pressure
  5. customthe residue was purified by silica gel column chromatography (ethyl acetate/hexane)

출처 및 근거

ORD 기록
ord-84ea37d28eca4c0cae1ea3a68209e9fe
출처 데이터셋
uspto-grants-2016_07
특허 번호
US09382188B2

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