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

HRID 1185023

反応式

HRID 1185023 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

HCID 594738282-(6-(tert-butyl)-8-fluoro-1-oxophthalazin-2(1H)-yl)-6-chlorobenzaldehyde収率 52%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

To a 10 mL round bottom flask were added 6-tert-butyl-8-fluoro-2H-phthalazin-1-one 101h (640 mg, 2.9 mmol), 2-chloro-6-fluorobenzaldehyde (506 mg, 3.2 mmol), and cesium carbonate (488 mg, 1.5 mmol). The flask was evacuated and backfilled with nitrogen three times then ethoxytrimethylsilane (684 mg, 5.8 mmol) and DMF (5 mL) were added to the reaction flask. The resulting mixture was heated to 60° C. After 4 h of stirring, the solution was allowed to cool down to ambient temperature and the reaction was quenched by addition of 2 mL of H2O drop-wise. The desired product started to precipitate from the DMF and water mixture. The solid was collected by filtration after cooling down to 5° C., and washed with DMF/water (2/1, 2 mL, pre-cooled to 6° C.) and H2O (2 mL). The filter cake was dried under vacuum oven at 65° C. for overnight to afford 519 mg (52%) of 101i as a yellow solid. MS: [M+H]+: 359

後処理

  1. customThe flask was evacuated
  2. temperatureto cool down to ambient temperature
  3. customthe reaction was quenched by addition of 2 mL of H2O drop-wise
  4. customto precipitate from the 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, 2 mL, pre-cooled to 6° C.) and H2O (2 mL)
  8. customThe filter cake was dried under vacuum oven at 65° C. for overnight

出典と根拠

ORDレコード
ord-8ebfaa65d5194547af59d7cfce91775c
出典データセット
uspto-grants-2014_03
特許番号
US08669251B2

関連ノート

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