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

HRID 1054824
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인쇄 미리보기

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HRID 1054824 반응식
[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
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참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 24386Thionyl Chloride용매

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온도
60 °C

실험 절차

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).

후처리

  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)

출처 및 근거

ORD 기록
ord-ef2ffae73d6f4bcc8a4e1fd49ef898d6
출처 데이터셋
uspto-grants-2016_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09394285B2

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