Methanol → HCID 59375101、化合物

HRID 661928ノート

反応式

HRID 661928 の反応式
[C:1]([C:4]1[CH:5]=[CH:6][C:7]([C:22]2[CH:27]=[CH:26][CH:25]=[CH:24][C:23]=2[F:28])=[C:8]2[C:16]=1[NH:15][C:14]1[CH:13]=[C:12]([C:17](OCC)=[O:18])[CH:11]=[CH:10][C:9]2=1)(=[O:3])[NH2:2].[H-].[Al+3].[Li+].[H-].[H-].[H-].CO.C(O)(C(F)(F)F)=O>C1COCC1.CCOC(C)=O>[F:28][C:23]1[CH:24]=[CH:25][CH:26]=[CH:27][C:22]=1[C:7]1[C:8]2[C:9]3[C:14](=[CH:13][C:12]([CH2:17][OH:18])=[CH:11][CH:10]=3)[NH:15][C:16]=2[C:4]([C:1]([NH2:2])=[O:3])=[CH:5][CH:6]=1

参加物

7

反応物 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 21226445Aluminium lithium hydride2 回HCID 59375158HCID 59375158、化合物

生成物 1

HCID 59375101HCID 59375101、化合物収率 108.4%

試薬・触媒・溶媒 2

HCID 8028Tetrahydrofuran溶媒HCID 8857Ethyl Acetate溶媒

実験手順

A solution of ethyl 8-carbamoyl-5-(2-fluorophenyl)-9H-carbazole-2-carboxylate (Example 3-12, 0.81 g, 2.152 mmol) in THF (26.9 mL) at 0° C. was treated with lithium aluminum hydride (1.0 M in THF, 3.01 mL, 3.01 mmol), and the mixture was stirred at rt for 5 h. Additional lithium aluminum hydride (1.3 mL, 1.3 mmol) was added and the mixture was stirred at rt overnight. The mixture was treated with methanol and TFA and diluted with EtOAc, washed with brine, dried and concentrated to provide impure 4-(2-fluorophenyl)-7-(hydroxymethyl)-9H-carbazole-1-carboxamide (0.78 g) contaminated with starting material. A small amount was purified by preparative HPLC to provide 4-(2-fluorophenyl)-7-(hydroxymethyl)-9H-carbazole-1-carboxamide, isolated as the TFA salt. 1H NMR (500 MHz, methanol-d4) δ 7.82 (1H, d, J=7.8 Hz), 7.51 (1H, s), 7.44-7.50 (1H, m), 7.42 (1H, td, J=7.5, 1.9 Hz), 7.25-7.30 (1H, m), 7.22 (1H, t, J=9.2 Hz), 7.05 (1H, d, J=8.3 Hz), 6.99 (1H, d, J=7.8 Hz), 6.85 (1H, dd, J=8.0, 1.4 Hz), 4.62 (2H, s). Mass spectrum m/z 334.9 (M+H)+.

後処理

  1. stirringthe mixture was stirred at rt overnight
  2. washwashed with brine
  3. customdried
  4. concentrationconcentrated

出典と根拠

ORDレコード
ord-58f46fa5e2384badb123954fd4226cea
出典データセット
uspto-grants-2011_12
特許番号
US08084620B2

反応ノート

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