Sodium Carbonate → HCID 10221627, compound

HRID 547701Notes

Reaction equation

HRID 547701 reaction equation
C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[C:24](=[O:42])[N:25]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:26]=[C:27]([C:29]2[CH:33]=[CH:32][S:31][C:30]=2[CH:34]=[O:35])[CH:28]=1)#[N:16].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1>[C:15]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:23]1[C:24](=[O:42])[N:25]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)[CH:26]=[C:27]([C:29]2[CH:33]=[CH:32][S:31][C:30]=2[CH2:34][OH:35])[CH:28]=1)#[N:16]

Participants

5

Reactant 3

HCID 10340Sodium CarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 10293257HCID 10293257, compound

Product 1

HCID 10221627HCID 10221627, compoundYield 79.6%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Sodium triacetoxyborohydride (10 mg) was added to a solution of 10 mg of 3-(2-cyanophenyl)-5-(2-formylthiophen-3-yl)-1-phenyl-1,2-dihydropyridin-2-one in 2 ml of tetrahydrofuran and the mixture was stirred for 1 hour. A 10% aqueous solution of sodium carbonate was added thereto, the mixture was extracted with ethyl acetate and the organic layer was washed with water and a saturated saline solution and dried over magnesium sulfate. The solvent was concentrated in vacuo and the residue was purified by an NH silica gel column chromatography to give 8 mg of the title compound as white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washthe organic layer was washed with water
  3. dry with materiala saturated saline solution and dried over magnesium sulfate
  4. concentrationThe solvent was concentrated in vacuo
  5. customthe residue was purified by an NH silica gel column chromatography

Sources & evidence

ORD record
ord-57b96813170e4c6e816f843292e9b982
Source dataset
uspto-grants-2011_05
Patent number
US07939549B2

Reaction notes

Loading…