Hydrogen Peroxide → HCID 59375146, 화합물

HRID 1811124노트

반응식

HRID 1811124 반응식
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:19]3[C:14](=[CH:15][C:16](C=O)=[CH:17][CH:18]=3)[NH:13][C:12]=2[C:11]([C:23]([NH2:25])=[O:24])=[CH:10][CH:9]=1.OO.S(=O)(=O)(O)[OH:29].[OH-].[Na+]>CO>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:19]3[C:14](=[CH:15][C:16]([OH:29])=[CH:17][CH:18]=3)[NH:13][C:12]=2[C:11]([C:23]([NH2:25])=[O:24])=[CH:10][CH:9]=1

참가 물질

6

반응물 4

HCID 784Hydrogen Peroxide2회HCID 1118Sulfuric Acid2회HCID 14798Sodium HydroxideHCID 86642953HCID 86642953, 화합물

생성물 1

HCID 59375146HCID 59375146, 화합물

시약·촉매·용매 1

HCID 887Methanol용매

실험 절차

Step 2 A solution of crude 4-(2-fluorophenyl)-7-formyl-9H-carbazole-1-carboxamide (25.2 mg, 0.076 mmol) in methanol (2 mL) at 0° C. was treated with 30% aqueous hydrogen peroxide (0.039 mL, 0.379 mmol) and sulfuric acid (0.020 mL, 0.379 mmol). After 1.5 h, additional hydrogen peroxide (0.100 mL) and sulfuric acid (0.050 mL) were added and the mixture was stirred at rt overnight. After 16 h, 1 M aqueous sodium hydroxide (2 mL) was added and the mixture was stirred for 1 h. The pH was adjusted to ca. 4 and the organic solvent was removed under vacuum. The aqueous residue was diluted with water and the precipitate was collected by filtration, washed with water and dried. The residue was purified by preparative HPLC to provide 4-(2-fluorophenyl)-7-hydroxy-9H-carbazole-1-carboxamide as tan solid after lypholization (5.1 mg, 21%). 1H NMR (400 MHz, methanol-d4) δ 7.81 (1H, d, J=7.70 Hz), 7.45-7.64 (2 H, m), 7.21-7.42 (2 H, m), 7.03 (1 H, d, J=7.92 Hz), 6.90-6.99 (2 H, m), 6.45 (1 H, dd, J=8.58, 2.20 Hz). Mass spectrum m/z 321.0 (M+H)+.

후처리

  1. waitAfter 16 h
  2. stirringthe mixture was stirred for 1 h
  3. customthe organic solvent was removed under vacuum
  4. additionThe aqueous residue was diluted with water
  5. filtrationthe precipitate was collected by filtration
  6. washwashed with water
  7. customdried
  8. customThe residue was purified by preparative HPLC

출처 및 근거

ORD 기록
ord-32e0c2a7881842b2b15992aa1ae46d6d
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08362065B2

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