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P-Cresol → 6-Chloro-5-(4-methoxyphenyl)-1H-indazole-3-carboxylic acid p-tolyl ester

HRID 1054824
ノート
印刷プレビュー

反応式

HRID 1054824 の反応式
[Cl:1][C:2]1[CH:10]=[C:9]2[C:5]([C:6]([C:11]([OH:13])=[O:12])=[N:7][NH:8]2)=[CH:4][C:3]=1[C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1.[CH:22]1[C:27](O)=[CH:26][CH:25]=[C:24]([CH3:29])[CH:23]=1.C(N(CC)CC)C>S(Cl)(Cl)=O>[C:24]1([CH3:29])[CH:25]=[CH:26][C:27]([O:12][C:11]([C:6]2[C:5]3[C:9](=[CH:10][C:2]([Cl:1])=[C:3]([C:14]4[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=4)[CH:4]=3)[NH:8][N:7]=2)=[O:13])=[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

5

反応物 3

HCID 2879P-CresolHCID 8471TriethylamineHCID 866987906-Chloro-5-(4-methoxyphenyl)-1H-indazole-3-carboxylic acid

生成物 1

HCID 866988166-Chloro-5-(4-methoxyphenyl)-1H-indazole-3-carboxylic acid p-tolyl ester収率 27%

試薬・触媒・溶媒 1

HCID 24386Thionyl Chloride溶媒

反応条件

温度
60 °C

実験手順

A mixture of 6-chloro-5-(4-methoxyphenyl)-1H-indazole-3-carboxylic acid (547 mg, 1.81 mmol) in thionyl chloride (10 mL) was heated to 60° C. for 4 hours, cooled to room temperature and concentrated in vacuo. The residue was dissolved in CH2Cl2 (20 mL) and treated with p-cresol (399 mg, 3.61 mmol) followed by triethylamine (369 mg, 3.61 mmol). The reaction mixture was stirred for 16 hours and quenched with water (20 mL). The layers were separated and the organic phase was concentrated in vacuo. The residue was purified by flash chromatography (25-50% EtOAc/heptane) to give the title compound (192 mg, 27% yield).

後処理

  1. temperaturecooled to room temperature
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was dissolved in CH2Cl2 (20 mL)
  4. customquenched with water (20 mL)
  5. customThe layers were separated
  6. concentrationthe organic phase was concentrated in vacuo
  7. customThe residue was purified by flash chromatography (25-50% EtOAc/heptane)

出典と根拠

ORDレコード
ord-ef2ffae73d6f4bcc8a4e1fd49ef898d6
出典データセット
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US09394285B2

反応ノート

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