Ethyl Acetate → [4-(3-Methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanol

HRID 1678796Notes

Reaction equation

HRID 1678796 reaction equation
[CH3:1][C:2]1[N:14]2[C:5]([C:6]3[CH:7]=[C:8]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:9]([C:15]4[CH:22]=[CH:21][C:18]([CH:19]=[O:20])=[CH:17][CH:16]=4)=[N:10][C:11]=3[CH:12]=[CH:13]2)=[N:4][N:3]=1.[BH4-].[Na+].C(OCC)(=O)C>CO>[CH3:1][C:2]1[N:14]2[C:5]([C:6]3[CH:7]=[C:8]([C:23]4[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=4)[C:9]([C:15]4[CH:16]=[CH:17][C:18]([CH2:19][OH:20])=[CH:21][CH:22]=4)=[N:10][C:11]=3[CH:12]=[CH:13]2)=[N:4][N:3]=1

Participants

5

Reactant 3

HCID 8857Ethyl AcetateHCID 4311764Sodium borohydrideHCID 594729414-(3-Methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzaldehyde

Product 1

HCID 15979643[4-(3-Methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)phenyl]methanol

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

To a solution of 4-(3-methyl-9-phenyl[1,2,4]triazolo[3,4-f]-1,6-naphthyridin-8-yl)benzaldehyde (5-2, 0.317 g, 0.870 mmol) in methanol (5 mL) was added sodium borohydride (0.033 g, 0.870 mmol) at 0° C. After 10 minutes, the reaction mixture was poured into ethyl acetate, and the organic layer was washed with a saturated solution of sodium bicarbonate, water, then brine, dried over sodium sulfate, filtered and concentrated to dryness under reduced pressure. Purification by reverse phase chromatography (Waters Sunfire MSC18, 1% acetonitrile/0.1% trifluoroacetic acid/water→95% acetonitrile/0.1% trifluoroacetic acid/water) gave the title compounds as a solid. HRMS (M+H+): calculated=367.1554, observed=367.1547.

Workup

  1. washthe organic layer was washed with a saturated solution of sodium bicarbonate, water
  2. dry with materialbrine, dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationconcentrated to dryness under reduced pressure
  5. customPurification by reverse phase chromatography (Waters Sunfire MSC18, 1% acetonitrile/0.1% trifluoroacetic acid/water→95% acetonitrile/0.1% trifluoroacetic acid/water)

Sources & evidence

ORD record
ord-34249ac51b7b48d591151540cfb524d5
Source dataset
uspto-grants-2011_08
Patent number
US08008317B2

Reaction notes

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