Ethanol → 8-Bromo-10-fluoro-2-hydroxy-9-trifluoromethyl-5,11-dihydro-6H-benzo[a]carbazole-3-carboxylic acid

HRID 1690670노트

반응식

HRID 1690670 반응식
C[O:2][C:3]([C:5]1[C:27]([OH:28])=[CH:26][C:8]2[C:9]3[NH:10][C:11]4[C:16]([C:17]=3[CH2:18][CH2:19][C:7]=2[CH:6]=1)=[CH:15][C:14]([Br:20])=[C:13]([C:21]([F:24])([F:23])[F:22])[C:12]=4[F:25])=[O:4].C(O)C.O.[Li+].[OH-]>C(OCC)(=O)C>[Br:20][C:14]1[CH:15]=[C:16]2[C:11](=[C:12]([F:25])[C:13]=1[C:21]([F:22])([F:23])[F:24])[NH:10][C:9]1[C:8]3[CH:26]=[C:27]([OH:28])[C:5]([C:3]([OH:4])=[O:2])=[CH:6][C:7]=3[CH2:19][CH2:18][C:17]2=1

참가 물질

6

반응물 4

HCID 702EthanolHCID 962WaterHCID 3939Lithium HydroxideHCID 160474068-Bromo-10-fluoro-2-hydroxy-9-trifluoromethyl-5,11-dihydro-6H-benzo[a]carbazole-3-carboxylic acid methyl ester

생성물 1

HCID 160474058-Bromo-10-fluoro-2-hydroxy-9-trifluoromethyl-5,11-dihydro-6H-benzo[a]carbazole-3-carboxylic acid수율 78.1%

시약·촉매·용매 1

HCID 8857Ethyl Acetate용매

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온도
50 °C

실험 절차

A sample of 8-Bromo-10-fluoro-2-hydroxy-9-trifluoromethyl-5,11-dihydro-6H-benzo[a]carbazole-3-carboxylic acid methyl ester (28.9 mg, 63.4 μmol) is treated with ethanol (0.3 mL) and water (0.5 mL) followed by LiOH (4 mg, 190 μmol). The reaction is then stirred at 50° C. overnight. The reaction is then diluted with ethyl acetate and extracted with 1 M HCl. The organics are then dried over MgSO4, filtered and the solvent is removed. The resulting residue is purified using a UV triggered HPLC to afford 22 mg of the title compound as a white solid; 1H NMR (400 MHz, MeOD) δ 7.78 (s, 1H), 7.76 (s, 1H), 7.32 (s, 1H), 3.00 (m, 2H), 2.95 (2, H); LC/MS calculated for [M+H]+ C18H11F4NO3: 445.1, found: 445.9.

후처리

  1. extractionextracted with 1 M HCl
  2. dry with materialThe organics are then dried over MgSO4
  3. filtrationfiltered
  4. customthe solvent is removed
  5. customThe resulting residue is purified

출처 및 근거

ORD 기록
ord-66d475668ef84e18bde2471905e3014f
출처 데이터셋
uspto-grants-2012_04
특허 번호
US08153671B2

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