4-Chloro-6,7-dimethoxyquinoline → 1-(4-(6,7-Dimethoxyquinolin-4-yloxy)-3-fluorophenyl)-4-(phenoxymethyl)pyrrolidin-2-one

HRID 1993378노트

반응식

HRID 1993378 반응식
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH3:15])=[C:9]([O:12][CH3:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.[F:16][C:17]1[CH:18]=[C:19]([N:24]2[CH2:28][CH:27]([CH2:29][O:30][C:31]3[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH2:26][C:25]2=[O:37])[CH:20]=[CH:21][C:22]=1[OH:23]>CN(C1C=CN=CC=1)C.C1(C)C=CC=CC=1.CCOC(C)=O>[CH3:13][O:12][C:9]1[CH:10]=[C:11]2[C:6](=[CH:7][C:8]=1[O:14][CH3:15])[N:5]=[CH:4][CH:3]=[C:2]2[O:23][C:22]1[CH:21]=[CH:20][C:19]([N:24]2[CH2:28][CH:27]([CH2:29][O:30][C:31]3[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=3)[CH2:26][C:25]2=[O:37])=[CH:18][C:17]=1[F:16]

참가 물질

6

반응물 2

HCID 4596104-Chloro-6,7-dimethoxyquinolineHCID 684205651-(3-Fluoro-4-hydroxyphenyl)-4-(phenoxymethyl)pyrrolidin-2-one

생성물 1

HCID 118576551-(4-(6,7-Dimethoxyquinolin-4-yloxy)-3-fluorophenyl)-4-(phenoxymethyl)pyrrolidin-2-one

시약·촉매·용매 3

HCID 142844-(Dimethylamino)pyridine촉매HCID 1140Toluene용매HCID 8857Ethyl Acetate용매

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온도
180 °C

실험 절차

A mixture of 4-chloro-6,7-dimethoxyquinoline (0.185 g, 0.83 mmol), 1-(3-fluoro-4-hydroxyphenyl)-4-(phenoxymethyl)pyrrolidin-2-one (Step 4, 250 mg, 0.83 mmol) and DMAP (101 mg, 0.83 mmol) in 8 mL of toluene (in a microwave tube) was heated in a microwave (Personal Chemistry, Emrys Optimizer) at 180° C. for 1.5 h. The mixture was cooled to RT and diluted with 50 mL of EtOAc. The solution was washed with 20 mL of satd. NaHCO3 followed by 20 mL of brine, dried over Na2SO4 and concentrated in vacuo. The residue was purified by chromatography (50% to 100% EtOAc/hexane) to provide the product as white solid. MS (ESI pos. ion) m/z: 489.3 (M+H). Calc'd Exact Mass for C28H25FN2O5: 488.51.

후처리

  1. temperatureThe mixture was cooled to RT
  2. washThe solution was washed with 20 mL of satd
  3. dry with materialdried over Na2SO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by chromatography (50% to 100% EtOAc/hexane)

출처 및 근거

ORD 기록
ord-26f27a7ce3c84ab6ab6f8455173d1dc9
출처 데이터셋
uspto-grants-2010_01
특허 번호
US07652009B2

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