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Potassium Carbonate → Ethyl 1-(3,4-difluorophenyl)-4[3-(ethoxycarbonyl)phenyl]-1H-pyrazole-3-carboxylate

HRID 587098
ノート
印刷プレビュー

反応式

HRID 587098 の反応式
Br[C:2]1[C:3]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:4][N:5]([C:7]2[CH:12]=[CH:11][C:10]([F:13])=[C:9]([F:14])[CH:8]=2)[CH:6]=1.CC1(C)C(C)(C)OB([C:28]2[CH:29]=[C:30]([CH:35]=[CH:36][CH:37]=2)[C:31]([O:33][CH3:34])=[O:32])O1.[C:39](=O)([O-])[O-].[K+].[K+]>C(O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:14][C:9]1[CH:8]=[C:7]([N:5]2[CH:6]=[C:2]([C:36]3[CH:37]=[CH:28][CH:29]=[C:30]([C:31]([O:33][CH2:34][CH3:39])=[O:32])[CH:35]=3)[C:3]([C:15]([O:17][CH2:18][CH3:19])=[O:16])=[N:4]2)[CH:12]=[CH:11][C:10]=1[F:13]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 27346513-Methoxycarbonylphenylboronic acid pinacol esterHCID 89464890ethyl 4-bromo-1-(3,4-difluorophenyl)-1H-pyrazole-3-carboxylate

生成物 1

HCID 89464679Ethyl 1-(3,4-difluorophenyl)-4[3-(ethoxycarbonyl)phenyl]-1H-pyrazole-3-carboxylate

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒
HCID 702Ethanol溶媒

実験手順

180 mg (0.54 mmol) of ethyl 4-bromo-1-(3,4-difluorophenyl)-1H-pyrazole-3-carboxylate, 156.7 mg (0.59 mmol) of methyl 3-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)benzoate, 158 mg (1.14 mmol) of potassium carbonate, 5.07 mg (0.011 mmol) of 2,2-dicyclohexylphosphino-2″,6″-diisopropoxybiphenyl and 1.22 mg (0.005 mmol) of palladium (II)acetate were suspended in 5 ml of ethanol and heated at the boil for 4 h. After cooling to room temperature, the solvent was removed under reduced pressure, the residue was dissolved in water and dichloromethane, the phases were separated and the organic phase was dried over magnesium sulfate. The crude product was purified by chromatography (ethyl acetate:n-heptane 1:4). This gave 84 mg (37%) of the desired product. 1H-NMR (400 MHz, CDCl3 δ, ppm) 8.15 (s, 1H); 8.05 (d, 1H); 7.96 (s, 1H); 7.74-7.69 (m, 2H); 7.53-7.47 (m, 2H); 7.28 (m, 1H); 4.48-4.34 (m, 4H); 1.43 (t, 3H); 1.29 (t, 3H)

後処理

  1. temperatureheated at the boil for 4 h
  2. customthe solvent was removed under reduced pressure
  3. dissolutionthe residue was dissolved in water
  4. customdichloromethane, the phases were separated
  5. dry with materialthe organic phase was dried over magnesium sulfate
  6. customThe crude product was purified by chromatography (ethyl acetate:n-heptane 1:4)

出典と根拠

ORDレコード
ord-d81fe33f664741ed9f685641a0ae0dee
出典データセット
uspto-grants-2016_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09226505B2

反応ノート

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