Triethylamine → 1h-Indazole-1-carboxylic acid,5-(chloromethyl)-3-(3-fluorophenyl)-,1,1-dimethylethyl ester

HRID 1610076노트

반응식

HRID 1610076 반응식
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:16]3[C:11](=[CH:12][CH:13]=[C:14]([CH2:17]O)[CH:15]=3)[N:10]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[N:9]=2)[CH:5]=[CH:6][CH:7]=1.C(N(CC)CC)C.CS([Cl:37])(=O)=O.C(OCC)(=O)C>C(Cl)Cl>[Cl:37][CH2:17][C:14]1[CH:15]=[C:16]2[C:11](=[CH:12][CH:13]=1)[N:10]([C:19]([O:21][C:22]([CH3:25])([CH3:24])[CH3:23])=[O:20])[N:9]=[C:8]2[C:4]1[CH:5]=[CH:6][CH:7]=[C:2]([F:1])[CH:3]=1

참가 물질

6

반응물 4

HCID 8471TriethylamineHCID 8857Ethyl AcetateHCID 31297Methanesulfonyl chlorideHCID 222608021h-Indazole-1-carboxylic acid,3-(3-fluorophenyl)-5-(hydroxymethyl)-,1,1-dimethylethyl ester

생성물 1

HCID 222606161h-Indazole-1-carboxylic acid,5-(chloromethyl)-3-(3-fluorophenyl)-,1,1-dimethylethyl ester

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

Under ice-cooling, to a solution of 3.0 g of tert-butyl 3-(3-fluorophenyl)-5-(hydroxymethyl)-1H-1-indazolecarboxylate in 30 ml methylene chloride were added 1.6 ml of triethylamine and 0.78 ml of methanesulfonyl chloride, and the mixture was stirred at room temperature for one day. To the reaction mixture was added 180 ml of ethyl acetate, and the mixture was sequentially washed with water, 1 N hydrochloric acid, water, saturated aqueous sodium hydrogencarbonate solution and brine, dried over anhydrous magnesium sulfate and the solvent was evaporated. The crude product was purified and separated by silica gel column chromatography (toluene), to give 2.74 g of the title compound as yellow crystals.

후처리

  1. washthe mixture was sequentially washed with water, 1 N hydrochloric acid, water, saturated aqueous sodium hydrogencarbonate solution and brine
  2. dry with materialdried over anhydrous magnesium sulfate
  3. customthe solvent was evaporated
  4. customThe crude product was purified
  5. customseparated by silica gel column chromatography (toluene)

출처 및 근거

ORD 기록
ord-50bbbb4a99c94fef82cbfc6f321ee738
출처 데이터셋
uspto-grants-2006_01
특허 번호
US06982274B2

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