Cesium carbonate → 2-(6-(tert-butyl)-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-chlorobenzaldehyde

HRID 2069714

반응식

HRID 2069714 반응식
[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[NH:10][N:9]=[CH:8]2)([CH3:4])([CH3:3])[CH3:2].[Cl:17][C:18]1[CH:25]=[CH:24][CH:23]=[C:22](F)[C:19]=1[CH:20]=[O:21].C(=O)([O-])[O-].[Cs+].[Cs+].C(O[Si](C)(C)C)C>CN(C=O)C>[C:1]([C:5]1[CH:6]=[C:7]2[C:12](=[C:13]([F:15])[CH:14]=1)[C:11](=[O:16])[N:10]([C:22]1[CH:23]=[CH:24][CH:25]=[C:18]([Cl:17])[C:19]=1[CH:20]=[O:21])[N:9]=[CH:8]2)([CH3:4])([CH3:2])[CH3:3]

참가 물질

6

반응물 4

HCID 10796Cesium carbonateHCID 15772EthoxytrimethylsilaneHCID 678472-Chloro-6-fluorobenzaldehydeHCID 594737656-(tert-Butyl)-8-fluorophthalazin-1(2H)-one

생성물 1

HCID 594738282-(6-(tert-butyl)-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-chlorobenzaldehyde수율 68.3%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a 3 L round bottom flask were added 6-tert-butyl-8-fluoro-2H-phthalazin-1-one (132.3 g, 0.6 mol), 2-chloro-6-fluorobenzaldehyde (104.8 g, 0.66 mol) and cesium carbonate (117.4 g, 0.36 mol). The flask was evacuated and backfilled with Nitrogen three times. Then, ethoxytrimethylsilane (142 g, 1.2 mol) and DMF (1.6 L) were added to the reaction flask, and the resulting mixture was heated to 60° C. After 4 h stirring, the solution was allowed to cool down to ambient temperature and the reaction was quenched by addition of 800 mL of H2O dropwise. The desired product started to precipitate from DMF and water mixture. The solid was collected by filtration after cooling down to 5° C., and washed with DMF/water (2/1, 750 mL, pre-cooled to 6° C.) and H2O (400 mL). The filter cake was dried under vacuum oven at 65° C. overnight to afford 147 g of the title compound (68.2% isolated yield) as a yellow solid. MS (ESI) 358, 360 (M+H)−.

후처리

  1. customThe flask was evacuated
  2. temperatureto cool down to ambient temperature
  3. customthe reaction was quenched by addition of 800 mL of H2O dropwise
  4. customto precipitate from DMF and water mixture
  5. filtrationThe solid was collected by filtration
  6. temperatureafter cooling down to 5° C.
  7. washwashed with DMF/water (2/1, 750 mL, pre-cooled to 6° C.) and H2O (400 mL)
  8. customThe filter cake was dried under vacuum oven at 65° C. overnight

출처 및 근거

ORD 기록
ord-396b71eb90a3446b87114a02d5c1a1a2
출처 데이터셋
uspto-grants-2012_10
특허 번호
US08299077B2

연결된 노트

불러오는 중…