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

HRID 931579Notes

Reaction equation

HRID 931579 reaction equation
[H-].[H-].[H-].[H-].[Li+].[Al+3].[N:7]([C:10]1([CH2:27][CH2:28][OH:29])[C:23]2[CH:22]=[C:21]([Cl:24])[N:20]=[C:19]([F:25])[C:18]=2[O:17][C:16]2[C:11]1=[CH:12][C:13]([Br:26])=[CH:14][CH:15]=2)=[N+]=[N-]>C1COCC1>[NH2:7][C:10]1([CH2:27][CH2:28][OH:29])[C:23]2[CH:22]=[C:21]([Cl:24])[N:20]=[C:19]([F:25])[C:18]=2[O:17][C:16]2[C:11]1=[CH:12][C:13]([Br:26])=[CH:14][CH:15]=2

Participants

4

Reactant 2

HCID 21226445Aluminium lithium hydrideHCID 866583662-(5-azido-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)ethanol

Product 1

HCID 866583632-(5-amino-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)ethanolYield 73.5%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

To a solution of LAH (1.0 M solution in tetrahydrafuran; 90 ml, 90 mmol) in THF (50 mL) at rt was added drop wise a solution of 2-(5-azido-7-bromo-3-chloro-1-fluoro-5H-chromeno[2,3-c]pyridin-5-yl)ethanol (24 g, 60.1 mmol) in THF (150 mL). The resulting mixture was stirred at RT for 1 h. The reaction mixture was quenched with sodiumsulfate decahydrate and stirred for 30 min. The mixture was filtered, the filtrate was 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 (16.5 g, 44.2 mmol) as a colorless oil.

Workup

  1. customThe reaction mixture was quenched with sodiumsulfate decahydrate
  2. stirringstirred for 30 min
  3. filtrationThe mixture was filtered
  4. concentrationthe filtrate was concentrated under reduced pressure
  5. customthe residue was purified by chromatography (0-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-dca4b0c325854cbea5d823b8b27e7497
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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