Water → 3-(4-fluorophenyl)-1H-indazole-5-carboxamide

HRID 1272752ノート

反応式

HRID 1272752 の反応式
C([N:4]1[C:12]2[C:7](=[CH:8][C:9]([C:13](Cl)=[O:14])=[CH:10][CH:11]=2)[C:6]([C:16]2[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=2)=[N:5]1)(=O)C.[OH-].[NH4+:24].O>C(Cl)Cl>[F:22][C:19]1[CH:20]=[CH:21][C:16]([C:6]2[C:7]3[C:12](=[CH:11][CH:10]=[C:9]([C:13]([NH2:24])=[O:14])[CH:8]=3)[NH:4][N:5]=2)=[CH:17][CH:18]=1

参加物

5

反応物 3

HCID 962WaterHCID 14923Ammonium HydroxideHCID 224802271-acetyl-3-(4-fluorophenyl)-1H-indazole-5-carbonyl chloride

生成物 1

HCID 99925193-(4-fluorophenyl)-1H-indazole-5-carboxamide収率 72%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

To a solution of 1-acetyl-3-(4-fluorophenyl)-1H-indazole-5-carbonyl chloride (200 mg, 0.63 mmol) in methylene chloride (20 mL) was added saturated ammonium hydroxide (NH4OH). The solution was stirred overnight at room temperature when it was added to water (100 mL) and extracted with ethyl acetate (3×40 mL). The combined organic layers were dried (Na2SO4) and concentrated under vacuo to an oil. The resulting oil was chromatographed on silica gel, eluting with 10% methanol in methylene chloride to give the title compound (115 mg, 72%). 1H NMR (DMSO-d6) δ 13.4 (s, 1H), 8.60 (s, 1H), 0.09 (m, 2H), 7.94 (d, 1H), 7.61 (d, 1H), 7.38 (t, 2H); ES-MS (m/z) 256 [M+1]+.

後処理

  1. extractionextracted with ethyl acetate (3×40 mL)
  2. dry with materialThe combined organic layers were dried (Na2SO4)
  3. concentrationconcentrated under vacuo to an oil
  4. customThe resulting oil was chromatographed on silica gel
  5. washeluting with 10% methanol in methylene chloride

出典と根拠

ORDレコード
ord-ec005101b9974c37b57658757e7924e9
出典データセット
uspto-grants-2007_04
特許番号
US07208513B2

反応ノート

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