Acetyl chloride → 2-(5-amino-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)ethanol

HRID 455579ノート

反応式

HRID 455579 の反応式
[Br:1][C:2]1[CH:3]=[C:4]2[C:15](=[CH:16][CH:17]=1)[O:14][C:7]1[C:8]([F:13])=[N:9][C:10]([Cl:12])=[CH:11][C:6]=1[C:5]2([NH:21]S(C(C)(C)C)=O)[CH2:18][CH2:19][OH:20].C(Cl)(=O)C>CO>[NH2:21][C:5]1([CH2:18][CH2:19][OH:20])[C:6]2[CH:11]=[C:10]([Cl:12])[N:9]=[C:8]([F:13])[C:7]=2[O:14][C:15]2[C:4]1=[CH:3][C:2]([Br:1])=[CH:17][CH:16]=2

参加物

4

反応物 2

HCID 6367Acetyl chlorideHCID 86658362N-(7-bromo-3-chloro-1-fluoro-5-(2-hydroxyethyl)-5H-chromeno[2,3-c]pyridin-5-yl)-2-methylpropane-2-sulfinamide

生成物 1

HCID 866583632-(5-amino-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)ethanol収率 88.2%

試薬・触媒・溶媒 1

HCID 887Methanol溶媒2 回

反応条件

温度
-20 °C

実験手順

To a solution of N-(7-bromo-3-chloro-1-fluoro-5-(2-hydroxyethyl)-5H-chromeno[2,3-c]pyridin-5-yl)-2-methylpropane-2-sulfinamide (5.8 g, 12.14 mmol) in dry MeOH (100 mL) at −20° C. was added a mixture of MeOH (80 mL)/acetylchloride (20 ml). The resulting reaction mixture was stirred at −20° C. for 30 min and then quenched with 10% aqueous solution of Na2CO3. DCM was added, the organic phase was separated and dried over Na2SO4. The solution concentrated under reduced pressure and the residue was purified by chromatography (0-50% EtOAc/hexanes) to afford 2-(5-amino-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)ethanol (4.0 g, 10.71 mmol, 88% yield) as a light yellow solid-foam.

後処理

  1. customThe resulting reaction mixture
  2. customquenched with 10% aqueous solution of Na2CO3
  3. additionDCM was added
  4. customthe organic phase was separated
  5. dry with materialdried over Na2SO4
  6. concentrationThe solution concentrated under reduced pressure
  7. customthe residue was purified by chromatography (0-50% EtOAc/hexanes)

出典と根拠

ORDレコード
ord-1a43a0f7c4e348c78bd918196b76edb4
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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