Aluminium lithium hydride → (5-amino-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)methanol

HRID 931585노트

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HRID 931585 반응식
[N:1]([C:4]1([CH2:21][OH:22])[C:17]2[CH:16]=[C:15]([Cl:18])[N:14]=[C:13]([F:19])[C:12]=2[O:11][C:10]2[C:5]1=[CH:6][C:7]([Br:20])=[CH:8][CH:9]=2)=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3]>C1COCC1>[NH2:1][C:4]1([CH2:21][OH:22])[C:17]2[CH:16]=[C:15]([Cl:18])[N:14]=[C:13]([F:19])[C:12]=2[O:11][C:10]2[C:5]1=[CH:6][C:7]([Br:20])=[CH:8][CH:9]=2

참가 물질

4

반응물 2

HCID 21226445Aluminium lithium hydrideHCID 86658369(5-azido-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)methanol

생성물 1

HCID 86658370(5-amino-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)methanol수율 93%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-10 °C

실험 절차

A solution of (5-azido-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)methanol (25.1 g, 65.1 mmol) in THF (500 mL) was cooled to −10° C. and a solution of LAH (1.0 M in THF; 65.1 mL, 65.1 mmol) was added drop wise via an addition funnel over a time period of 1.5 hours. Upon complete addition, the reaction mixture was stirred additional 20 min at −10° C. The reaction mixture was quenched with the drop wise addition of saturated aqueous potassium sodium tartarate solution (60 mL). The reaction was diluted with water and EtOAc. The organic layer was separated, washed with brine and dried over sodium sulfate. The solvent was removed under reduced pressure to afford (5-amino-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)methanol (21.74 g, 60.5 mmol, 93% yield).

후처리

  1. additionUpon complete addition
  2. customThe reaction mixture was quenched with the drop wise addition of saturated aqueous potassium sodium tartarate solution (60 mL)
  3. additionThe reaction was diluted with water and EtOAc
  4. customThe organic layer was separated
  5. washwashed with brine
  6. dry with materialdried over sodium sulfate
  7. customThe solvent was removed under reduced pressure

출처 및 근거

ORD 기록
ord-de364d0f44a54fb3bfe6a51192b15384
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09296759B2

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