Potassium Phosphate, Tribasic → HCID 16063512、化合物

HRID 1993926ノート

反応式

HRID 1993926 の反応式
Br[C:2]1[C:3](=[O:24])[N:4]([C:17]2[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=2)[N:5]([CH3:16])[C:6]=1[CH2:7][CH2:8][C:9]1[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=1.[CH:25]1(B(O)O)[CH2:27][CH2:26]1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1>O.CCOC(C)=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(C)C=CC=CC=1>[CH:25]1([C:2]2[C:3](=[O:24])[N:4]([C:17]3[CH:22]=[CH:21][C:20]([F:23])=[CH:19][CH:18]=3)[N:5]([CH3:16])[C:6]=2[CH2:7][CH2:8][C:9]2[CH:14]=[CH:13][C:12]([F:15])=[CH:11][CH:10]=2)[CH2:27][CH2:26]1

参加物

8

反応物 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 2760897Cyclopropylboronic acidHCID 686775324-Bromo-2-(4-fluoro-phenyl)-5-[2-(4-fluoro-phenyl)-ethyl]-1-methyl-1,2-dihydro-pyrazol-3-one

生成物 1

HCID 16063512HCID 16063512、化合物収率 19.6%

試薬・触媒・溶媒 3

HCID 167845palladium(II) acetate触媒HCID 1140Toluene溶媒HCID 22728543Water ethylacetate溶媒

反応条件

温度
100 °C

実験手順

Into a sealable tube under argon was added 4-bromo-2-(4-fluoro-phenyl)-5-[2-(4-fluoro-phenyl)-ethyl]-1-methyl-1,2-dihydro-pyrazol-3-one (0.312 g), cyclopropylboronic acid (0.139 g), potassium phosphate (0.924 g), tricyclohexyl phosphine (0.034 g) and toluene (3.0 mL). To this was added palladium acetate (0.013 g) and the tube was sealed and stirred at 100° C. for 20 hours. The reaction vessel was then cooled and the diluted with water/EtOAc. The phases were separated and the aqueous phase was extracted with further EtOAc. The combined organic phases were washed with brine, dried over sodium sulfate and evaporated in vacuo to afford a crude residue. Flash column chromatography over silica gel using ISCO combiflash chromatography and eluting with EtOAc/heptane afforded the desired 4-cyclopropyl-2-(4-fluoro-phenyl)-5-[2-(4-fluoro-phenyl)-ethyl]-1-methyl-1,2-dihydro-pyrazol-3-one (0.055 g) as a white crystalline solid. MS (ESI+): 315.1 ([M+H]+).

後処理

  1. customthe tube was sealed
  2. temperatureThe reaction vessel was then cooled
  3. customThe phases were separated
  4. extractionthe aqueous phase was extracted with further EtOAc
  5. washThe combined organic phases were washed with brine
  6. dry with materialdried over sodium sulfate
  7. customevaporated in vacuo
  8. customto afford a crude residue
  9. washFlash column chromatography over silica gel using ISCO combiflash chromatography and eluting with EtOAc/heptane

出典と根拠

ORDレコード
ord-10f73f28b734455d811820ab9c4362b1
出典データセット
uspto-grants-2010_01
特許番号
US07652057B2

反応ノート

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