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 931571노트

반응식

HRID 931571 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

반응 조건

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-b97239f34047495aba891c970f6b58f5
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296759B2

반응 노트

불러오는 중…