Sodium borohydride → HCID 68524433, compound

HRID 884116Notes

Reaction equation

HRID 884116 reaction equation
[F:1][C:2]([F:29])([F:28])[C:3]1[CH:27]=[CH:26][C:6]([CH:7]=[N:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=3)=[N:13][CH:14]=2)=[CH:5][CH:4]=1.[BH4-].[Na+]>CO>[F:28][C:2]([F:1])([F:29])[C:3]1[CH:27]=[CH:26][C:6]([CH2:7][NH:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]3[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=3)=[N:13][CH:14]=2)=[CH:5][CH:4]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 68525979HCID 68525979, compound

Product 1

HCID 68524433HCID 68524433, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Methyl 4-{5-[(4-trifluoromethylbenzylidene)-amino]pyridin-2-yloxy}benzoate (2.64 g, 6.59 mmol) was suspended in methanol (25 mL), and to the resulting suspension was slowly added sodium borohydride (1.25 g, 33.0 mmol). The resulting solution was stirred at room temperature for 3 days. The reaction solution was concentrated under reduced pressure. To the residue was added ethyl acetate, and washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, and evaporated. The residue was washed with diethyl ether, to thereby yield 2.65 g of the title compound.

Workup

  1. concentrationThe reaction solution was concentrated under reduced pressure
  2. additionTo the residue was added ethyl acetate
  3. washwashed with water and brine
  4. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  5. customevaporated
  6. washThe residue was washed with diethyl ether

Sources & evidence

ORD record
ord-257934ffaeb24c418a2858b8c93e85c1
Source dataset
uspto-grants-2012_08
Patent number
US08236826B2

Reaction notes

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