Sodium Sulfate → HCID 86761965, compound

HRID 931592Notes

Reaction equation

HRID 931592 reaction equation
[N:1]([C:4]1([CH:20]([CH3:23])[CH2:21][OH:22])[C:17]2[CH:16]=[C:15]([Cl:18])[N:14]=[CH:13][C:12]=2[O:11][C:10]2[C:5]1=[CH:6][C:7]([Br:19])=[CH:8][CH:9]=2)=[N+]=[N-].[H-].[H-].[H-].[H-].[Li+].[Al+3].[O-]S([O-])(=O)=O.[Na+].[Na+]>C1COCC1>[NH2:1][C:4]1([CH:20]([CH3:23])[CH2:21][OH:22])[C:17]2[CH:16]=[C:15]([Cl:18])[N:14]=[CH:13][C:12]=2[O:11][C:10]2[C:5]1=[CH:6][C:7]([Br:19])=[CH:8][CH:9]=2

Participants

5

Reactant 3

HCID 24436Sodium SulfateHCID 21226445Aluminium lithium hydrideHCID 86761964HCID 86761964, compound

Product 1

HCID 86761965HCID 86761965, compoundYield 70%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 2-(5-azido-7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-yl)propan-1-ol (1300 mg, 3.29 mmol, 85% purity) in THF (10 mL) was cooled to 0° C. under nitrogen atmosphere. LAH (1.0M solution in THF; 3.61 mL, 3.61 mmol) was added dropwise. A mixture of celite and Na2SO4*10H2O was added. The reaction mixture was filtered, the solvent was removed under reduced pressure and the residue was purified by flash chromatography (10-50% EtOAc/hexanes) to afford the desired product 2-(5-amino-7-bromo-3-chloro-5H-chromeno[2,3-c]pyridin-5-yl)propan-1-ol (0.85 g, 2.300 mmol, 70.0% yield) as a white solid.

Workup

  1. additionwas added
  2. filtrationThe reaction mixture was filtered
  3. customthe solvent was removed under reduced pressure
  4. customthe residue was purified by flash chromatography (10-50% EtOAc/hexanes)

Sources & evidence

ORD record
ord-2d806b68f01245d6b2fdaf652dc1fac2
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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