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

HRID 1049590

反応式

HRID 1049590 の反応式
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

参加物

9

反応物 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 1317360334-((Tert-butyl(dimethyl)silyl)oxy)-2'-fluoro-5'-methoxybiphenyl-2-yl trifluoromethanesulfonate

生成物 1

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

試薬・触媒・溶媒 4

HCID 167845palladium(II) acetate触媒HCID 887Methanol溶媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
100 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-84ea37d28eca4c0cae1ea3a68209e9fe
出典データセット
uspto-grants-2016_07
特許番号
US09382188B2

関連ノート

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