Benzyl Chloride → 3-Benzyloxy-6-chloro-5,9-diaza-benzo[c]fluoren-7-one

HRID 1840420노트

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HRID 1840420 반응식
[Cl:1][C:2]1[C:14]2[C:13](=[O:15])[C:12]3[CH:11]=[N:10][CH:9]=[CH:8][C:7]=3[C:6]=2[C:5]2[CH:16]=[CH:17][C:18]([OH:20])=[CH:19][C:4]=2[N:3]=1.[CH2:21](Cl)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C.ClCCl>[CH2:21]([O:20][C:18]1[CH:17]=[CH:16][C:5]2[C:6]3[C:7]4[CH:8]=[CH:9][N:10]=[CH:11][C:12]=4[C:13](=[O:15])[C:14]=3[C:2]([Cl:1])=[N:3][C:4]=2[CH:19]=1)[C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1

참가 물질

6

반응물 3

HCID 7503Benzyl ChlorideHCID 11430Potassium CarbonateHCID 1357900736-Chloro-3-hydroxy-5,9-diaza-benzo[c]fluoren-7-one

생성물 1

HCID 234480493-Benzyloxy-6-chloro-5,9-diaza-benzo[c]fluoren-7-one

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

반응 조건

온도
90 °C

실험 절차

6-Chloro-3-hydroxy-5,9-diaza-benzo[c]fluoren-7-one (Example 34a) (27 mg) was dissolved in DMF (2 ml). To the solution were added benzyl chloride (0.016 ml) and potassium carbonate (29 mg). The mixture was stirred at 90° C. for 2 hours. The reaction mixture was dissolved in dichloromethane and the mixture was washed with water. The organic layer was dried over anhydrous sodium sulfate and evaporated to dryness. The residue was purified by silica gel column chromatography developed by dichloromethane and dichloromethane-MeOH=50:1. The desired product (12 mg) was obtained as a light yellow solid. EI−MS: m/z 372 (M+); 1H-NMR (CDCl3): δ5.25 (2H, s), 7.30-7.55 (7H, m), 8.00 (1H, dd, J=5 Hz, 1 Hz), 8.36 (1H, d, J=9Hz), 8.95 (1H, d, 5 Hz), 9.03 (1H, d, J=1 Hz).

후처리

  1. washthe mixture was washed with water
  2. dry with materialThe organic layer was dried over anhydrous sodium sulfate
  3. customevaporated to dryness
  4. customThe residue was purified by silica gel column chromatography

출처 및 근거

ORD 기록
ord-e47788040ab948c296139d9c99a7fbad
출처 데이터셋
uspto-grants-2004_01
특허 번호
US06680326B2

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