Sodium Bicarbonate → HCID 22646584、化合物

HRID 393601

反応式

HRID 393601 の反応式
Cl[C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1.C(=O)([O-])O.[Na+].[CH2:24]([O:31][C:32]1[C:33]([CH3:40])=[CH:34][C:35]([F:39])=[C:36]([OH:38])[CH:37]=1)[C:25]1[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=1.CC(C)([O-])C.[K+]>CS(C)=O.O>[CH2:24]([O:31][C:32]1[C:33]([CH3:40])=[CH:34][C:35]([F:39])=[C:36]([CH:37]=1)[O:38][C:2]1[C:11]2[C:6](=[CH:7][C:8]([O:14][CH2:15][CH2:16][O:17][CH3:18])=[C:9]([C:12]#[N:13])[CH:10]=2)[N:5]=[CH:4][CH:3]=1)[C:25]1[CH:26]=[CH:27][CH:28]=[CH:29][CH:30]=1

参加物

7

反応物 4

HCID 516892Sodium BicarbonateHCID 219910495-Benzyloxy-2-fluoro-4-methylphenolHCID 22646522HCID 22646522、化合物HCID 23665647Potassium tert-butoxide

生成物 1

HCID 22646584HCID 22646584、化合物収率 63%

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
160 °C

実験手順

4-Chloro-6-cyano-7-(2-methoxyethoxy)quinoline (187 mg, 0.71 mmol), (prepared as described for the starting material in Example 1 but with an aqueous sodium hydrogen carbonate work up), was added to a solution of 5-benzyloxy-2-fluoro-4-methylphenol (248 mg, 1 mmol), (prepared as described for the starting material in Example 3), and potassium t-butoxide (120 mg, 1 mmol) in DMSO (5 ml) and the mixture then heated at 160° C. for 1.5 hours. The mixture was diluted with water and extracted with ethyl acetate. The organic layer was separated, washed with brine, dried (MgSO4) and the solvent removed by evaporation. The residue was purified by column chromatography eluting with methylene chloride/ethyl acetate (55/45) followed by preparative reverse-phase HPLC eluting with aqueous ammonium carbonate (2 g/1, adjusted to pH7 with carbon dioxide) and methanol (20/80) to give 4-(5-benzyloxy-2-fluoro-4-methylphenoxy)-6-cyano-7-(2-methoxyethoxy)quinoline (204 mg, 63%).

後処理

  1. custom(prepared
  2. extractionextracted with ethyl acetate
  3. customThe organic layer was separated
  4. washwashed with brine
  5. dry with materialdried (MgSO4)
  6. customthe solvent removed by evaporation
  7. customThe residue was purified by column chromatography
  8. washeluting with methylene chloride/ethyl acetate (55/45)
  9. washeluting with aqueous ammonium carbonate (2 g/1, adjusted to pH7 with carbon dioxide) and methanol (20/80)

出典と根拠

ORDレコード
ord-694d6787e78e4946aa91d24d25588844
出典データセット
uspto-grants-2004_10
特許番号
US06809097B1

関連ノート

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