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

HRID 1690670ノート

反応式

HRID 1690670 の反応式
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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-66d475668ef84e18bde2471905e3014f
出典データセット
uspto-grants-2012_04
特許番号
US08153671B2

反応ノート

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