Sodium Methoxide → 1-(2,4-Dimethoxybenzyl)-4-(3-fluorophenyl)-6-methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile

HRID 640716ノート

反応式

HRID 640716 の反応式
[C:1]([CH2:3][C:4]([N:6]([CH2:24][C:25]1[CH:30]=[CH:29][C:28]([O:31][CH3:32])=[CH:27][C:26]=1[O:33][CH3:34])[C:7]1[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][C:8]=1[C:15](=O)[C:16]1[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=1)=[O:5])#[N:2].C[O-].[Na+]>CO>[CH3:34][O:33][C:26]1[CH:27]=[C:28]([O:31][CH3:32])[CH:29]=[CH:30][C:25]=1[CH2:24][N:6]1[C:7]2[C:8](=[CH:9][C:10]([O:13][CH3:14])=[CH:11][CH:12]=2)[C:15]([C:16]2[CH:21]=[CH:20][CH:19]=[C:18]([F:22])[CH:17]=2)=[C:3]([C:1]#[N:2])[C:4]1=[O:5]

参加物

4

反応物 2

HCID 10942334Sodium MethoxideHCID 686597692-Cyano-N-(2,4-dimethoxybenzyl)-N-[2-(3-fluorobenzoyl)-4-methoxyphenyl]acetamide

生成物 1

HCID 112707271-(2,4-Dimethoxybenzyl)-4-(3-fluorophenyl)-6-methoxy-2-oxo-1,2-dihydroquinoline-3-carbonitrile

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

実験手順

To solution of 2-cyano-N-(2,4-dimethoxybenzyl)-N-[2-(3-fluorobenzoyl)-4-methoxyphenyl]acetamide (56.0 mg, 0.121 mmol) in 1 mL of methanol was added sodium methoxide solution in methanol (0.083 mL of 4.37 M, 0.363 mmol). The solution was heated to reflux for 5 minutes, then cooled to room temperature. The reaction was partitioned between EtOAc and water, and the organic layer was washed with brine, dried over Na2SO4, filtered, and concentrated in vacuo. The crude residue was purified by flash chomatography through SiO2 (30-50% EtOAc/hexane) to provide the titled product as a yellow foam. 1H-NMR (500 MHz, CDCl3) δ 7.56-7.60 (m, 1H), 7.39 (d, J=9.5 Hz, 1H), 7.25-7.31 (m, 2H), 7.17-7.21 (m, 2H), 6.91 (d, J=8.5 Hz, 1H), 6.74 (br s, 1H), 6.52 (br s, 1H), 6.38 (br d, J=8.5 Hz, 1H), 5.54 (s, 2H), 3.95 (s, 3H), 3.77 (s, 3H), 3.67 (s, 3H) ppm. HRMS (ES) exact mass calculated for C26H22FN2O4 (M+H+): 445.1558. Found 445.1574.

後処理

  1. temperatureThe solution was heated
  2. temperatureto reflux for 5 minutes
  3. customThe reaction was partitioned between EtOAc and water
  4. washthe organic layer was washed with brine
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified by flash chomatography through SiO2 (30-50% EtOAc/hexane)

出典と根拠

ORDレコード
ord-f35df93158f54b06b7583044eeda59b3
出典データセット
uspto-grants-2010_04
特許番号
US07692017B2

反応ノート

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