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

HRID 1993378ノート

反応式

HRID 1993378 の反応式
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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 142844-(Dimethylamino)pyridine触媒HCID 1140Toluene溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
180 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-26f27a7ce3c84ab6ab6f8455173d1dc9
出典データセット
uspto-grants-2010_01
特許番号
US07652009B2

反応ノート

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