Cesium carbonate → 7-(Benzyloxy)-4-(2-fluoro-4-nitrophenoxy)-6-methoxyquinoline

HRID 15514노트

반응식

HRID 15514 반응식
[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13](=[O:19])[CH:14]=[CH:15][NH:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[F:28][C:29]1[CH:30]=[C:31]([N+:36]([O-:38])=[O:37])[CH:32]=[CH:33][C:34]=1F>CN(C=O)C.CC#N>[CH2:1]([O:8][C:9]1[CH:18]=[C:17]2[C:12]([C:13]([O:19][C:34]3[CH:33]=[CH:32][C:31]([N+:36]([O-:38])=[O:37])=[CH:30][C:29]=3[F:28])=[CH:14][CH:15]=[N:16]2)=[CH:11][C:10]=1[O:20][CH3:21])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 1230531,2-Difluoro-4-nitrobenzeneHCID 226465797-(Benzyloxy)-6-methoxyquinolin-4-ol

생성물 1

HCID 229354107-(Benzyloxy)-4-(2-fluoro-4-nitrophenoxy)-6-methoxyquinoline수율 46%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6342Acetonitrile용매

실험 절차

A mixture of 7-(benzyloxy)-6-methoxyquinolin-4(1H)-one (4.4 g, 15.6 mmol), Cs2CO3 (9.0 g) in DMF (40 mL) and CH3CN (40 mL) was stirred for 30 minutes at rt. To this mixture was added 3,4-difluoronitrobenzene (2.5 g, 15.7 mmol), and the reaction mixture was stirred at rt overnight. The reaction product was a mixture of O- and N-alkylation products. It was mostly concentrated in vacuo, EtOAc (200 mL) and water (50 mL) were added to the residue, EtOAc layer was separated, dried over MgSO4 and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluting with hexane:EtOAc:MeOH/800:200:40, and then 700:300:40 to obtain the desired O-alkylation product (3.0 mg, 46%) as a white solid. 1H NMR (CDCl3) δ 8.73 (d, 1H, J=6.0 Hz), 8.29-8.26 (m, 2H), 8.08 (s, 1H), 7.60-7.35 (m, 7H), 6.67 (d, 1H, J=6.6 Hz), 5.42 (s, 2H), 4.10 (s, 3H); MS(ESI+) m/z 421.3 (M+H)+.

후처리

  1. stirringthe reaction mixture was stirred at rt overnight
  2. additiona mixture of O- and N-alkylation products
  3. concentrationIt was mostly concentrated in vacuo, EtOAc (200 mL) and water (50 mL)
  4. additionwere added to the residue, EtOAc layer
  5. customwas separated
  6. dry with materialdried over MgSO4
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified by flash column chromatography on silica gel eluting with hexane

출처 및 근거

ORD 기록
ord-53f3a8859bef4310abbe4cc2d5d65160
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07732613B2

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