Sodium borohydride → 5-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(3,4-difluorophenyl)-furo[2,3-b]pyridin-3-ol

HRID 8803Notes

Reaction equation

HRID 8803 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[CH:9]=[C:10]3[C:24](=[O:25])[C:23]([C:30]4[CH:35]=[CH:34][C:33]([F:36])=[C:32]([F:37])[CH:31]=4)(C(OC)=O)[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:4][CH:3]=1.[BH4-].[Na+]>CCO>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:9]=[C:10]3[C:24]([OH:25])=[C:23]([C:30]4[CH:35]=[CH:34][C:33]([F:36])=[C:32]([F:37])[CH:31]=4)[O:22][C:11]3=[N:12][C:13]=2[C:14]2[CH:19]=[CH:18][C:17]([Cl:20])=[CH:16][C:15]=2[Cl:21])=[CH:6][CH:7]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 21984819Methyl 5-(4-chlorophenyl)-6-(2,4-dichlorophenyl)-2-(3,4-difluorophenyl)-3-oxo-2,3-dihydrofuro[2,3-b]pyridine-2-carboxylate

Product 1

HCID 103913755-(4-Chlorophenyl)-6-(2,4-dichlorophenyl)-2-(3,4-difluorophenyl)-furo[2,3-b]pyridin-3-ol

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of 80 mg (0.14 mmol) of the product of Step B dissolved in 1 mL EtOH was added 9 mg (0.20 mmol) of sodium borohydride. The reaction mixture was stirred at RT for 5 min then partitioned between EtOAc and water. The organic layer was separated, dried (MgSO4), filtered and evaporated. The residue was then redissolved in 10 mL MeOH and 2 mL of a 2.0 N solution of sodium hydroxide was added. The reaction mixture was stirred at 80° C. for 0.5 h, then cooled to room temperature and partitioned between EtOAc and 10% aq. NaHSO4. The organic layer was separated, washed with water, dried (MgSO4), filtered and evaporated. The residue was purified on a silica gel flash chromatography column eluted with 0–20% EtOAc-hexane. Combination of the purified fractions and drying in vacuo afforded the title compound.

Workup

  1. customthen partitioned between EtOAc and water
  2. customThe organic layer was separated
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customevaporated
  6. dissolutionThe residue was then redissolved in 10 mL MeOH
  7. addition2 mL of a 2.0 N solution of sodium hydroxide was added
  8. stirringThe reaction mixture was stirred at 80° C. for 0.5 h
  9. temperaturecooled to room temperature
  10. custompartitioned between EtOAc and 10% aq. NaHSO4
  11. customThe organic layer was separated
  12. washwashed with water
  13. dry with materialdried (MgSO4)
  14. filtrationfiltered
  15. customevaporated
  16. customThe residue was purified on a silica gel flash chromatography column
  17. washeluted with 0–20% EtOAc-hexane
  18. customCombination of the purified fractions and drying in vacuo

Sources & evidence

ORD record
ord-5e1c4faac4c241878ca727421cfe449d
Source dataset
uspto-grants-2006_08
Patent number
US07091216B2

Reaction notes

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