Potassium Carbonate → HCID 68525583, compound

HRID 1932527Notes

Reaction equation

HRID 1932527 reaction equation
Cl.Cl.[Cl:3][C:4]1[CH:5]=[C:6]([CH:33]=[CH:34][C:35]=1[Cl:36])[C:7]([NH:9][C:10]1[CH:11]=[N:12][C:13]([O:16][C:17]2[CH:22]=[CH:21][C:20]([C:23]([N:25]3[CH2:30][CH2:29][CH:28]([NH:31][CH3:32])[CH2:27][CH2:26]3)=[O:24])=[CH:19][CH:18]=2)=[CH:14][CH:15]=1)=[O:8].Br[CH2:38][C:39]1[CH:44]=[CH:43][C:42]([F:45])=[C:41]([F:46])[CH:40]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[Cl:3][C:4]1[CH:5]=[C:6]([CH:33]=[CH:34][C:35]=1[Cl:36])[C:7]([NH:9][C:10]1[CH:11]=[N:12][C:13]([O:16][C:17]2[CH:18]=[CH:19][C:20]([C:23]([N:25]3[CH2:30][CH2:29][CH:28]([NH:31][CH2:32][CH2:38][C:39]4[CH:44]=[CH:43][C:42]([F:45])=[C:41]([F:46])[CH:40]=4)[CH2:27][CH2:26]3)=[O:24])=[CH:21][CH:22]=2)=[CH:14][CH:15]=1)=[O:8]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 5814364-(Bromomethyl)-1,2-difluorobenzeneHCID 68522239HCID 68522239, compound

Product 1

HCID 68525583HCID 68525583, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3,4-dichloro-N-{6-[4-(4-methylamino-piperidine-1-carbonyl)phenoxy]pyridin-3-yl}benzamide dihydrochloride (114 mg, 0.2 mmol) was dissolved in DMF (3 mL). To the resulting solution were added 4-bromomethyl-1,2-difluorobenzene (31 μl, 0.24 mmol) and potassium carbonate (111 mg, 0.8 mmol), and this solution was stirred for 4 hours at room temperature. The resulting reaction solution was concentrated under reduced pressure. The residue was diluted with ethyl acetate and washed with water and brine. The organic layer was dried over anhydrous magnesium sulfate, and evaporated. This residue was purified by silica gel column chromatography (chloroform:methanol=50:1), to thereby yield 60 mg of the title compound.

Workup

  1. customThe resulting reaction solution
  2. concentrationwas concentrated under reduced pressure
  3. additionThe residue was diluted with ethyl acetate
  4. washwashed with water and brine
  5. dry with materialThe organic layer was dried over anhydrous magnesium sulfate
  6. customevaporated
  7. customThis residue was purified by silica gel column chromatography (chloroform:methanol=50:1)

Sources & evidence

ORD record
ord-1ffaad16b7d74763990db02e544d2b24
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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