Potassium Carbonate → HCID 18458608, compound

HRID 2304877Notes

Reaction equation

HRID 2304877 reaction equation
[OH:1][C:2]1[C:7]([C:8](=[O:12])[CH:9]([CH3:11])[CH3:10])=[CH:6][N:5]=[C:4]2[S:13][C:14]([C:17]3[CH:22]=[CH:21][C:20]([NH:23][C:24](=[O:28])[CH:25]([CH3:27])[CH3:26])=[CH:19][CH:18]=3)=[C:15]([CH3:16])[C:3]=12.C(=O)([O-])[O-].[K+].[K+].[F:35][C:36]1[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[C:37]=1[CH2:38]Br>CN(C)C=O>[F:35][C:36]1[CH:43]=[CH:42][CH:41]=[C:40]([F:44])[C:37]=1[CH2:38][N:5]1[CH:6]=[C:7]([C:8](=[O:12])[CH:9]([CH3:11])[CH3:10])[C:2](=[O:1])[C:3]2[C:15]([CH3:16])=[C:14]([C:17]3[CH:18]=[CH:19][C:20]([NH:23][C:24](=[O:28])[CH:25]([CH3:27])[CH3:26])=[CH:21][CH:22]=3)[S:13][C:4]1=2

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5814352-(Bromomethyl)-1,3-difluorobenzeneHCID 178422060HCID 178422060, compound

Product 1

HCID 18458608HCID 18458608, compoundYield 91%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

The compound obtained in Example 28 (1 g), potassium carbonate (0.349 g) and N,N-dimethylformamide (5 ml) were mixed and 2,6-difluorobenzyl bromide (0.783 g) was added and the reaction mixture was stirred at room temperature overnight (15 hours). The reaction mixture was concentrated under reduced pressure to obtain a residue, which was partitioned between ethyl acetate-methyl ethyl ketone and water, and the aqueous layer was extracted with ethylacetate. The organic layers were combined and washed with a saturated saline and then dried over anhydrous magnesium sulfate. The residue obtained after concentration was washed with diisopropylether to obtain the title compound (1.2 g, 91.0%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customto obtain a residue, which
  3. customwas partitioned between ethyl acetate-methyl ethyl ketone and water
  4. extractionthe aqueous layer was extracted with ethylacetate
  5. washwashed with a saturated saline
  6. dry with materialdried over anhydrous magnesium sulfate
  7. customThe residue obtained
  8. concentrationafter concentration
  9. washwas washed with diisopropylether

Sources & evidence

ORD record
ord-fd60607af3254f609c0d5f498e360788
Source dataset
uspto-grants-2002_08
Patent number
US06437132B2

Reaction notes

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