Sodium Carbonate → (2,3-Dihydrobenzo[1,4]oxazin-4-yl)[3-(4-fluoro-2-(trifluoromethyl)phenyl)-2,5-dihydropyrrol-1-yl]methanone

HRID 551826

反応式

HRID 551826 の反応式
[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([C:11]([N:13]2[CH2:17][CH:16]=[C:15](B3OC(C)(C)C(C)(C)O3)[CH2:14]2)=[O:12])[CH2:3][CH2:2]1.Br[C:28]1[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=1[C:35]([F:38])([F:37])[F:36].C(=O)([O-])[O-].[Na+].[Na+]>O.COCCOC>[O:1]1[C:6]2[CH:7]=[CH:8][CH:9]=[CH:10][C:5]=2[N:4]([C:11]([N:13]2[CH2:17][CH:16]=[C:15]([C:28]3[CH:33]=[CH:32][C:31]([F:34])=[CH:30][C:29]=3[C:35]([F:36])([F:38])[F:37])[CH2:14]2)=[O:12])[CH2:3][CH2:2]1

参加物

6

反応物 3

HCID 10340Sodium CarbonateHCID 5209832-Bromo-5-fluorobenzotrifluorideHCID 67187569(2,3-Dihydrobenzo[1,4]oxazin-4-yl)[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,5-dihydropyrrol-1-yl]methanone

生成物 1

HCID 67187504(2,3-Dihydrobenzo[1,4]oxazin-4-yl)[3-(4-fluoro-2-(trifluoromethyl)phenyl)-2,5-dihydropyrrol-1-yl]methanone収率 70.4%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 80711,2-Dimethoxyethane溶媒

実験手順

0.4 g of (2,3-dihydrobenzo[1,4]oxazin-4-yl)[3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-2,5-dihydropyrrol-1-yl]methanone, 0.4 g of 1-bromo-4-fluoro-2-(trifluoromethyl)benzene, 1.4 ml of a 2N solution of sodium carbonate in water and 15 ml of ethylene glycol dimethyl ether are placed in a 100 ml three-necked flask equipped with a magnetic stirrer and placed under an inert atmosphere. The reaction mixture is degassed with nitrogen for 30 minutes and then the reaction mixture is heated at reflux for 14 h. After filtering and concentrating to dryness, the crude reaction product obtained is chromatographed on silica gel, elution being carried out with a gradient of ethyl acetate in dichloromethane varying from 0% to 10%. 0.31 g of (2,3-dihydrobenzo[1,4]oxazin-4-yl)[3-(4-fluoro-2-(trifluoromethyl)phenyl)-2,5-dihydropyrrol-1-yl]methanone is obtained.

後処理

  1. customequipped with a magnetic stirrer
  2. customThe reaction mixture is degassed with nitrogen for 30 minutes
  3. temperaturethe reaction mixture is heated
  4. temperatureat reflux for 14 h
  5. filtrationAfter filtering
  6. concentrationconcentrating to dryness
  7. customthe crude reaction product
  8. customobtained
  9. customis chromatographed on silica gel, elution

出典と根拠

ORDレコード
ord-21d0623101a14257861d5146c451eddd
出典データセット
uspto-grants-2011_05
特許番号
US07947834B2

関連ノート

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