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

HRID 931585ノート

反応式

HRID 931585 の反応式
[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

参加物

4

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-10 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-de364d0f44a54fb3bfe6a51192b15384
出典データセット
uspto-grants-2016_03
特許番号
US09296759B2

反応ノート

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