Potassium Carbonate → HCID 67333397、化合物

HRID 1804820ノート

反応式

HRID 1804820 の反応式
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([OH:11])=[CH:3][CH:2]=1.Br[CH2:13][C:14]1[CH:15]=[CH:16][C:17]([F:24])=[C:18]([CH:23]=1)[C:19]([O:21][CH3:22])=[O:20].C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:24][C:17]1[CH:16]=[CH:15][C:14]([CH2:13][N:1]2[C:10]3[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=3)[C:4](=[O:11])[CH:3]=[CH:2]2)=[CH:23][C:18]=1[C:19]([O:21][CH3:22])=[O:20]

参加物

5

反応物 3

HCID 11430Potassium CarbonateHCID 22645461Methyl 5-(bromomethyl)-2-fluorobenzoateHCID 178516385quinolin-4-ol

生成物 1

HCID 67333397HCID 67333397、化合物

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

A mixture of quinolin-4-ol, methyl 5-(bromomethyl)-2-fluorobenzoate (prepared as described in US 2007/0021427 A1, 1 eq) and potassium carbonate (1.2 eq) in dry DMF (0.1 M solution) was stirred at 100° C. for 1 h. After solvent evaporation, the residue was dissolved in DCM and washed twice with H2O and once with brine. The organic phase was dried over Na2SO4 and concentrated to dryness under reduced pressure. The resulting crude was purified by flash-chromatography (EtOAc/PE 9:1) to give the title compound. The O-alkylated isomer is eluted before the title compound.

後処理

  1. customAfter solvent evaporation
  2. dissolutionthe residue was dissolved in DCM
  3. washwashed twice with H2O and once with brine
  4. dry with materialThe organic phase was dried over Na2SO4
  5. concentrationconcentrated to dryness under reduced pressure
  6. customThe resulting crude was purified by flash-chromatography (EtOAc/PE 9:1)

出典と根拠

ORDレコード
ord-82638a5427384b5290c151f5c9ff24a0
出典データセット
uspto-grants-2013_01
特許番号
US08354413B2

反応ノート

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