7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-one → tert-butyl 2-(7-bromo-3-chloro-1-fluoro-5-hydroxy-5H-chromeno[2,3-c]pyridin-5-yl)acetate

HRID 455584ノート

反応式

HRID 455584 の反応式
[Cl-].[C:2]([O:6][C:7](=[O:10])[CH2:8][Zn+])([CH3:5])([CH3:4])[CH3:3].[Br:11][C:12]1[CH:13]=[C:14]2[C:25](=[CH:26][CH:27]=1)[O:24][C:17]1[C:18]([F:23])=[N:19][C:20]([Cl:22])=[CH:21][C:16]=1[C:15]2=[O:28]>C1COCC1>[Br:11][C:12]1[CH:13]=[C:14]2[C:25](=[CH:26][CH:27]=1)[O:24][C:17]1[C:18]([F:23])=[N:19][C:20]([Cl:22])=[CH:21][C:16]=1[C:15]2([CH2:8][C:7]([O:6][C:2]([CH3:5])([CH3:4])[CH3:3])=[O:10])[OH:28]

参加物

4

反応物 2

HCID 574756427-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-oneHCID 178451183HCID 178451183、化合物

生成物 1

HCID 86658364tert-butyl 2-(7-bromo-3-chloro-1-fluoro-5-hydroxy-5H-chromeno[2,3-c]pyridin-5-yl)acetate収率 89%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
0 °C

実験手順

To a solution of (2-tert-butoxy-2-oxoethyl)zinc(II) chloride (0.5M in Et2O; 670 ml, 335 mmol) at 0° C. was added drop wise a solution of 7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-one (55 g, 167 mmol) in THF (30 mL). The resulting reaction mixture was stirred at 0° C. for 1 h. The reaction mixture was quenched with aqueous, saturated NH4Cl solution and extracted with EtOAc. The organic extracts were dried over Na2SO4 and concentrated under reduced pressure to afford tert-butyl 2-(7-bromo-3-chloro-1-fluoro-5-hydroxy-5H-chromeno[2,3-c]pyridin-5-yl)acetate (66.0 g, 148 mmol, 89% yield) as a yellow solid.

後処理

  1. customThe resulting reaction mixture
  2. customThe reaction mixture was quenched with aqueous, saturated NH4Cl solution
  3. extractionextracted with EtOAc
  4. dry with materialThe organic extracts were dried over Na2SO4
  5. concentrationconcentrated under reduced pressure

出典と根拠

ORDレコード
ord-4e792dbb382b45a38801417c412482d2
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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