Methanol → HCID 59375101, 화합물

HRID 661928노트

반응식

HRID 661928 반응식
[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

참가 물질

7

반응물 4

HCID 887MethanolHCID 6422Trifluoroacetic acidHCID 21226445Aluminium lithium hydride2회HCID 59375158HCID 59375158, 화합물

생성물 1

HCID 59375101HCID 59375101, 화합물수율 108.4%

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매HCID 8857Ethyl Acetate용매

실험 절차

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)+.

후처리

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

출처 및 근거

ORD 기록
ord-58f46fa5e2384badb123954fd4226cea
출처 데이터셋
uspto-grants-2011_12
특허 번호
US08084620B2

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