Potassium Carbonate → 1h-Pyrazole-3-carboxamide,4-[3-(hydroxymethyl)phenyl]-1-[(4-methoxyphenyl)methyl]-n-phenyl-

HRID 20323

反応式

HRID 20323 の反応式
[C:1]1([NH:7][C:8]([C:10]2[C:14](I)=[CH:13][N:12]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[N:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[OH:31][CH2:32][C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1>C(O)C.C1(C)C=CC=CC=1.O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[C:1]1([NH:7][C:8]([C:10]2[C:14]([C:37]3[CH:36]=[CH:35][CH:34]=[C:33]([CH2:32][OH:31])[CH:38]=3)=[CH:13][N:12]([CH2:16][C:17]3[CH:22]=[CH:21][C:20]([O:23][CH3:24])=[CH:19][CH:18]=3)[N:11]=2)=[O:9])[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1

参加物

6

反応物 3

HCID 11430Potassium CarbonateHCID 2734662[3-(Hydroxymethyl)phenyl]boronic acidHCID 668573141h-Pyrazole-3-carboxamide,4-iodo-1-[(4-methoxyphenyl)methyl]-n-phenyl-

生成物 1

HCID 668554221h-Pyrazole-3-carboxamide,4-[3-(hydroxymethyl)phenyl]-1-[(4-methoxyphenyl)methyl]-n-phenyl-収率 131.9%

試薬・触媒・溶媒 2

HCID 178418851HCID 178418851、化合物触媒HCID 86587398Ethanol toluene water溶媒

反応条件

温度
120 °C

実験手順

A mixture of 4-iodo-1-(4-methoxy-benzyl)-1H-pyrazole-3-carboxylic acid phenylamide (50 mg; 0.11 mmol), bis(tri-tert-butylphosphine)palladium (12 mg), potassium carbonate (100 mg; 0.66 mmol) and 3-(hydroxymethyl)benzene boronic acid (21 mg; 0.14 mmol) in ethanol/toluene/water (4 ml:1 ml:1 ml) was heated at 120° C. (50 W) for 15 minutes in a CEM Discover microwave synthesiser. The reaction was evaporated and the residue partitioned between ethyl acetate and brine. The ethyl acetate layer was separated, dried (MgSO4), filtered and evaporated and the crude material purified by flash column chromatography eluting with 1:2 then 2:1 ethyl acetate/hexane. Product containing fractions were combined and evaporated to give 60 mg of 4-(3-hydroxymethyl-phenyl)-1-(4-methoxy-benzyl)-1H-pyrazole-3-carboxylic acid phenylamide.

後処理

  1. customThe reaction was evaporated
  2. customthe residue partitioned between ethyl acetate and brine
  3. customThe ethyl acetate layer was separated
  4. dry with materialdried (MgSO4)
  5. filtrationfiltered
  6. customevaporated
  7. customthe crude material purified by flash column chromatography
  8. washeluting with 1:2
  9. additionProduct containing fractions
  10. customevaporated

出典と根拠

ORDレコード
ord-40de71f74413494b89cc56d776bab3ea
出典データセット
uspto-grants-2010_06
特許番号
US07745638B2

関連ノート

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