Aluminium lithium hydride → (5-amino-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)methanol
Reaction equation
[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]=2Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
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).
Workup
- additionUpon complete addition
- customThe reaction mixture was quenched with the drop wise addition of saturated aqueous potassium sodium tartarate solution (60 mL)
- additionThe reaction was diluted with water and EtOAc
- customThe organic layer was separated
- washwashed with brine
- dry with materialdried over sodium sulfate
- customThe solvent was removed under reduced pressure
Sources & evidence
- ORD record
- ord-de364d0f44a54fb3bfe6a51192b15384
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09296759B2
Reaction notes
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