Sodium borohydride → HCID 67777123, compound

HRID 1026242Notes

Reaction equation

HRID 1026242 reaction equation
[BH4-].[Na+].[Br:3][C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH:12]2[CH2:14][CH2:13]2)[CH:7]=[CH:6][C:5]=1[CH2:15][C:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][Si:25]([CH:32]([CH3:34])[CH3:33])([CH:29]([CH3:31])[CH3:30])[CH:26]([CH3:28])[CH3:27])=[CH:20][N:19]=1)=[O:17]>C(O)C>[Br:3][C:4]1[CH:9]=[C:8]([O:10][CH2:11][CH:12]2[CH2:13][CH2:14]2)[CH:7]=[CH:6][C:5]=1[CH2:15][CH:16]([C:18]1[CH:23]=[CH:22][C:21]([O:24][Si:25]([CH:29]([CH3:31])[CH3:30])([CH:26]([CH3:28])[CH3:27])[CH:32]([CH3:33])[CH3:34])=[CH:20][N:19]=1)[OH:17]

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 67778223HCID 67778223, compound

Product 1

HCID 67777123HCID 67777123, compoundYield 80.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

Sodium borohydride (0.109 g) was added to a solution of 2-[2-bromo-4-(cyclopropylmethoxy)phenyl]-1-(5-{[tris(1-methylethyl)silyl]oxy}pyridin-2-yl)ethanone (1.50 g) in ethanol (10 mL) at room temperature. The reaction mixture was stirred at room temperature for 1 hr, and the solvent was evaporated under reduced pressure. The residue was diluted with ethyl acetate and water, and the organic layer was separated. The organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound (1.210 g).

Workup

  1. customthe solvent was evaporated under reduced pressure
  2. additionThe residue was diluted with ethyl acetate and water
  3. customthe organic layer was separated
  4. washThe organic layer was washed with saturated brine
  5. dry with materialdried over anhydrous magnesium sulfate
  6. customthe solvent was evaporated under reduced pressure
  7. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-7528aebe87cf427e91d2ac5eb4905963
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

Loading…