Cesium fluoride → Methyl 3-chloro-4-(2,4-difluorophenyl)quinoline-6-carboxylate

HRID 533398ノート

反応式

HRID 533398 の反応式
Br[C:2]1[C:11]2[C:6](=[CH:7][CH:8]=[C:9]([C:12]([O:14][CH3:15])=[O:13])[CH:10]=2)[N:5]=[CH:4][C:3]=1[Cl:16].[F:17][C:18]1[CH:23]=[C:22]([F:24])[CH:21]=[CH:20][C:19]=1OB(O)O.[F-].[Cs+].O1CCOCC1>[Pd].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].O>[Cl:16][C:3]1[CH:4]=[N:5][C:6]2[C:11]([C:2]=1[C:21]1[CH:20]=[CH:19][C:18]([F:17])=[CH:23][C:22]=1[F:24])=[CH:10][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:8][CH:7]=2

参加物

7

反応物 4

HCID 25953Cesium fluorideHCID 312751,4-DioxaneHCID 222378292,4-Difluorophenylboric acidHCID 67773454Methyl 4-bromo-3-chloroquinoline-6-carboxylate

生成物 1

HCID 67773515Methyl 3-chloro-4-(2,4-difluorophenyl)quinoline-6-carboxylate収率 69.3%

試薬・触媒・溶媒 2

HCID 178506421HCID 178506421、化合物触媒HCID 962Water溶媒2 回

反応条件

温度
100 °C

実験手順

Under argon gas atmosphere, a mixture of methyl 4-bromo-3-chloroquinoline-6-carboxylate (130 mg), 2,4-difluorophenylboric acid (137 mg), a 1,1′-bis(diphenylphosphino)ferrocene palladium (H) dichloride/dichloromethane complex (177 mg), cesium fluoride (197 mg), 1,4-dioxane (8 mL), and water (2 mL) was heated under stirring in an oil bath at 100° C. for one day. The reaction mixture was returned to room temperature, and water was added, and extracted with ethyl acetate. The organic layer was concentrated under reduced pressure, and the resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate) to obtain methyl 3-chloro-4-(2,4-difluorophenyl)quinoline-6-carboxylate (100 mg).

後処理

  1. customwas returned to room temperature
  2. extractionextracted with ethyl acetate
  3. concentrationThe organic layer was concentrated under reduced pressure
  4. customthe resulting residue was purified under silica gel column chromatography (hexane/ethyl acetate)

出典と根拠

ORDレコード
ord-777a251daad84671af204320cfc450bb
出典データセット
uspto-grants-2014_10
特許番号
US08853242B2

反応ノート

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