Water → Methyl 6-(trifluoromethyl)-1H-indazole-3-carboxylate

HRID 2108945ノート

反応式

HRID 2108945 の反応式
[CH3:1][O:2][C:3](=[O:19])[CH2:4][C:5]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:6]=1[NH:15]C(=O)C.[N:20](OC(C)(C)C)=O.O>C(O)(=O)C>[CH3:1][O:2][C:3]([C:4]1[C:5]2[C:6](=[CH:7][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:9][CH:10]=2)[NH:15][N:20]=1)=[O:19]

参加物

5

反応物 3

HCID 962WaterHCID 10906Tert-Butyl nitriteHCID 57633614(2-Acetylamino-4-trifluoromethylphenyl)-acetic acid methyl ester

生成物 1

HCID 53408454Methyl 6-(trifluoromethyl)-1H-indazole-3-carboxylate

試薬・触媒・溶媒 1

HCID 176Acetic Acid溶媒

反応条件

温度
95 °C

実験手順

To a solution of (2-acetylamino-4-trifluoromethylphenyl)-acetic acid methyl ester (16 g, 0.058 mol) in acetic acid (50 mL) was added dropwise t-butyl nitrite (90%) (7.35 g, 0.063 mol) over a period of 20 min. at 90-95° C. The mixture was then stirred for 0.5 h at 95° C., poured into cold water and stirred for 1 h. The precipitates were collected by filtration and washed with water. The crude material was dissolved in ethyl acetate and dried over sodium sulfate. The solvent was removed in vacuo. This material (13.4 g, 95%) was used without further purification in the next step. A small sample was crystallized from ethyl acetate to yield a white solid, mp 240-242° C. 1H NMR (DMSO-d-6) 8.25 (d, J=8.5 Hz, 1H), 8.04 (s, 1H), 7.58 (d, J=8.5 Hz, 1H), 3.95 (s, 3H). MS (FAB) m/z: 245.1 (M++1).

後処理

  1. stirringstirred for 1 h
  2. filtrationThe precipitates were collected by filtration
  3. washwashed with water
  4. dissolutionThe crude material was dissolved in ethyl acetate
  5. dry with materialdried over sodium sulfate
  6. customThe solvent was removed in vacuo
  7. customThis material (13.4 g, 95%) was used without further purification in the next step
  8. customA small sample was crystallized from ethyl acetate
  9. customto yield a white solid, mp 240-242° C

出典と根拠

ORDレコード
ord-d637fa0db9114d579861c5e83b4f1477
出典データセット
uspto-grants-2009_04
特許番号
US07514463B2

反応ノート

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