Cesium carbonate → 7-bromo-1-fluoro-3-(neopentyloxy)-5H-chromeno[2,3-c]pyridin-5-one

HRID 455699ノート

反応式

HRID 455699 の反応式
[Br:1][C:2]1[CH:3]=[CH:4][C:5](F)=[C:6]([C:8]([C:10]2[CH:15]=[C:14]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])[N:13]=[C:12]([F:22])[C:11]=2[O:23]COC)=[O:9])[CH:7]=1.B(Br)(Br)Br.[Cl-].[NH4+].C(=O)([O-])[O-].[Cs+].[Cs+]>C(Cl)Cl.C(#N)C.O>[Br:1][C:2]1[CH:7]=[C:6]2[C:5](=[CH:4][CH:3]=1)[O:23][C:11]1[C:12]([F:22])=[N:13][C:14]([O:16][CH2:17][C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:15][C:10]=1[C:8]2=[O:9]

参加物

8

反応物 4

HCID 10796Cesium carbonateHCID 25134Boron tribromideHCID 25517Ammonium ChlorideHCID 67383169(5-Bromo-2-fluorophenyl)(2-fluoro-3-(methoxymethoxy)-6-(neopentyloxy)pyridin-4-yl)methanone

生成物 1

HCID 673828597-bromo-1-fluoro-3-(neopentyloxy)-5H-chromeno[2,3-c]pyridin-5-one収率 78.6%

試薬・触媒・溶媒 3

HCID 962Water溶媒2 回HCID 6342Acetonitrile溶媒HCID 6344Dichloromethane溶媒2 回

実験手順

A solution of (5-bromo-2-fluorophenyl)(2-fluoro-3-(methoxymethoxy)-6-(neopentyloxy)pyridin-4-yl)methanone (1.89 g, 4.25 mmol) in DCM (20 mL) was cooled to −78° C. under nitrogen atmosphere. Boron tribromide (1.0M in CH2Cl2; 4.25 mL, 4.25 mmol) was added drop wise and the reaction mixture was stirred for 5 min at rt. Aqueous, saturated ammonium chloride solution was added, followed by water and DCM. The organic phase was separated and dried over magnesium sulfate. The solvent was removed under reduced pressure to afford a yellow solid, which was dissolved in ACN (20.00 mL). Cesium carbonate (1.386 g, 4.25 mmol) was added in one portion and the reaction mixture was allowed to stir for 5 min. Water was added and the remaining light-yellow solid was filtered off and dried to afford 7-bromo-1-fluoro-3-(neopentyloxy)-5H-chromeno[2,3-c]pyridin-5-one (1.27 g).

後処理

  1. customThe organic phase was separated
  2. dry with materialdried over magnesium sulfate
  3. customThe solvent was removed under reduced pressure
  4. customto afford a yellow solid, which
  5. stirringto stir for 5 min
  6. filtrationthe remaining light-yellow solid was filtered off
  7. customdried

出典と根拠

ORDレコード
ord-00c5125f7aa044e5b708969161754882
出典データセット
uspto-grants-2013_07
特許番号
US08497264B2

反応ノート

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