N-(7-bromo-3-chloro-1-fluoro-5-(2-hydroxyethyl)-5H-chromeno[2,3-c]pyridin-5-yl)-2-methylpropane-2-sulfinamide → 2-(5-amino-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)ethanol

HRID 931627노트

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HRID 931627 반응식
[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]>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

참가 물질

3

반응물 1

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

생성물 1

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

시약·촉매·용매 1

HCID 887Methanol용매2회

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온도
-20 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-8e7c29120f78462ebdc8682f7bc4fb0a
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296759B2

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