Sodium borohydride → 6-(5-Hydroxymethyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-nicotinonitrile

HRID 1514729Notes

Reaction equation

HRID 1514729 reaction equation
[CH:1]([C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:4]=1[CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][N:17]=1)=[O:2].[BH4-].[Na+]>CO>[OH:2][CH2:1][C:3]1[O:7][N:6]=[C:5]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][N:9]=2)[C:4]=1[CH2:14][O:15][C:16]1[CH:23]=[CH:22][C:19]([C:20]#[N:21])=[CH:18][N:17]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydride2×HCID 866462576-(5-Formyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-nicotinonitrile

Product 1

HCID 667181586-(5-Hydroxymethyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-nicotinonitrileYield 94.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

A suspension of 6-(5-formyl-3-pyridin-2-yl-isoxazol-4-ylmethoxy)-nicotinonitrile (0.77 g, 2.5 mmol) in methanol (20 mL) was cooled in an ice bath and treated with sodium borohydride (0.29 g, 7.7 mmol). The reaction mixture was allowed to reach room temperature and was stirred for 72 h. Additional sodium borohydride (0.29 g, 7.7 mmol) was added and stirring at room temperature was continued for 3 h. After quenching with methanol all volatile components were evaporated. The residue was partitioned (ethyl acetate/brine). The organic layer was dried (Na2SO4), filtered and concentrated to afford the title compound (0.73 g, 94%) as a brown solid. MS: m/e=309.2 [M+H]+.

Workup

  1. temperaturewas cooled in an ice bath
  2. customto reach room temperature
  3. stirringstirring at room temperature
  4. waitwas continued for 3 h
  5. customAfter quenching with methanol all volatile components
  6. customwere evaporated
  7. customThe residue was partitioned (ethyl acetate/brine)
  8. dry with materialThe organic layer was dried (Na2SO4)
  9. filtrationfiltered
  10. concentrationconcentrated

Sources & evidence

ORD record
ord-62a7057596d84e458d503c4253b05296
Source dataset
uspto-grants-2012_07
Patent number
US08222246B2

Reaction notes

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