Potassium Carbonate → HCID 67333397, 화합물

HRID 1804820노트

반응식

HRID 1804820 반응식
[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]

참가 물질

5

반응물 3

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

생성물 1

HCID 67333397HCID 67333397, 화합물

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-82638a5427384b5290c151f5c9ff24a0
출처 데이터셋
uspto-grants-2013_01
특허 번호
US08354413B2

반응 노트

불러오는 중…