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Potassium Carbonate → (4-Fluorophenyl)methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-(1-methyl-1H-pyrazol-4-yl)benzoate

HRID 1623738
ノート
印刷プレビュー

反応式

HRID 1623738 の反応式
Br[C:2]1[CH:3]=[CH:4][C:5]([O:19][CH2:20][C:21]2[CH:26]=[CH:25][C:24]([F:27])=[CH:23][CH:22]=2)=[C:6]([CH:18]=1)[C:7]([O:9][CH2:10][C:11]1[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=1)=[O:8].[CH3:28][N:29]1[CH:33]=[C:32](B2OC(C)(C)C(C)(C)O2)[CH:31]=[N:30]1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:27][C:24]1[CH:25]=[CH:26][C:21]([CH2:20][O:19][C:5]2[CH:4]=[CH:3][C:2]([C:32]3[CH:31]=[N:30][N:29]([CH3:28])[CH:33]=3)=[CH:18][C:6]=2[C:7]([O:9][CH2:10][C:11]2[CH:16]=[CH:15][C:14]([F:17])=[CH:13][CH:12]=2)=[O:8])=[CH:22][CH:23]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

7

反応物 3

HCID 11430Potassium CarbonateHCID 27739871-Methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazoleHCID 67107744(4-Fluorophenyl)methyl 5-bromo-2-{[(4-fluorophenyl)methyl]oxy}benzoate

生成物 1

HCID 68108578(4-Fluorophenyl)methyl 2-{[(4-fluorophenyl)methyl]oxy}-5-(1-methyl-1H-pyrazol-4-yl)benzoate

試薬・触媒・溶媒 3

HCID 178418397
HCID 178418397、化合物
触媒
HCID 962Water溶媒
HCID 312751,4-Dioxane溶媒

反応条件

温度
90 °C

実験手順

A mixture of (4-fluorophenyl)methyl 5-bromo-2-{[(4-fluorophenyl)methyl]oxy}benzoate (420 mg, 0.97 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (208 mg, 1.00 mmol), tetrakis(triphenylphosphine)palladium(0) (34.7 mg, 0.03 mmol) and K2CO3 (414 mg, 3 mmol) in 1,4-dioxane (10 ml) and water (2 ml) was stirred under nitrogen and heated at 90° C. for 16 hours. The solvent was removed, and the residue was dissolved in ethyl acetate (100 ml) and filtered. The filtrate was washed with water (50 ml) and brine (50 ml), dried over Na2SO4, and concentrated to give the crude product. The crude product was purified by a silica gel column (eluting with dichloromethane/methanol=50:1) yield the title compound as a white solid. 360 mg.

後処理

  1. customThe solvent was removed
  2. dissolutionthe residue was dissolved in ethyl acetate (100 ml)
  3. filtrationfiltered
  4. washThe filtrate was washed with water (50 ml) and brine (50 ml)
  5. dry with materialdried over Na2SO4
  6. concentrationconcentrated
  7. customto give the crude product
  8. customThe crude product was purified by a silica gel column (eluting with dichloromethane/methanol=50:1)

出典と根拠

ORDレコード
ord-342f02be307b4d6e9b2bba1c7d6dd4e1
出典データセット
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08778939B2

反応ノート

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