Hydrogen Peroxide → HCID 86761962, compound

HRID 931590Notes

Reaction equation

HRID 931590 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1[CH:8]=[N:9][C:10]([Cl:12])=[CH:11][C:6]=1[C:5]2([C:18]([CH3:20])=[CH2:19])[OH:17].B.C1C[O:25]CC1.[OH-].[Na+].OO>C1COCC1.O.CCOCC>[Br:1][C:2]1[CH:3]=[C:4]2[C:14](=[CH:15][CH:16]=1)[O:13][C:7]1[CH:8]=[N:9][C:10]([Cl:12])=[CH:11][C:6]=1[C:5]2([CH:18]([CH3:20])[CH2:19][OH:25])[OH:17]

Participants

8

Reactant 4

HCID 784Hydrogen PeroxideHCID 14798Sodium HydroxideHCID 2723981Borane;tetrahydrofuranHCID 86761963HCID 86761963, compound

Product 1

HCID 86761962HCID 86761962, compoundYield 75.2%

Reagents, catalysts & solvents 3

HCID 962WaterSolvent2×HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 7-bromo-3-chloro-5-(prop-1-en-2-yl)-5H-chromeno[2,3-c]pyridin-5-ol (3.2 g, 9.08 mmol) in THF (80 mL) was added a solution of borane-THF complex (1.0M in THF; 72.6 mL, 72.6 mmol) at RT under nitrogen atmosphere. The reaction mixture was allowed to stir at RT overnight. Water (10 mL) was added, followed by 2 M NaOH (15 mL). Then hydrogen peroxide (35 wt. % solution in H2O; 22.25 mL, 726 mmol) was added slowly. Et2O was added, followed by water. The organic phase was separated, washed with brine and dried over MgSO4. The solvent was removed under reduced pressure and the residue was purified by flash chromatography (5-30% EtOAc/hexanes). The desired product 7-bromo-3-chloro-5-(1-hydroxypropan-2-yl)-5H-chromeno[2,3-c]pyridin-5-ol (2.53 g, 6.83 mmol, 75% yield) was isolated as a white solid (1:1 mixture of diastereoisomers).

Workup

  1. customThe organic phase was separated
  2. washwashed with brine
  3. dry with materialdried over MgSO4
  4. customThe solvent was removed under reduced pressure
  5. customthe residue was purified by flash chromatography (5-30% EtOAc/hexanes)

Sources & evidence

ORD record
ord-4cf5cd25f0ae4b69812600679b4e2360
Source dataset
uspto-grants-2016_03
Patent number
US09296759B2

Reaction notes

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