3-Hydroxypyridine → HCID 68783006, compound

HRID 2266002Notes

Reaction equation

HRID 2266002 reaction equation
Cl[C:2]1[C:7]([CH:8]=[CH:9][C:10]([NH:12][CH2:13][C:14]2[CH:19]=[CH:18][C:17]([NH:20][S:21]([CH3:24])(=[O:23])=[O:22])=[C:16]([F:25])[CH:15]=2)=[O:11])=[CH:6][CH:5]=[C:4]([C:26]([F:29])([F:28])[F:27])[N:3]=1.[OH:30][C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C=O)C>[F:25][C:16]1[CH:15]=[C:14]([CH:19]=[CH:18][C:17]=1[NH:20][S:21]([CH3:24])(=[O:23])=[O:22])[CH2:13][NH:12][C:10](=[O:11])[CH:9]=[CH:8][C:7]1[C:2]([O:30][C:31]2[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=2)=[N:3][C:4]([C:26]([F:29])([F:28])[F:27])=[CH:5][CH:6]=1

Participants

5

Reactant 3

HCID 79713-HydroxypyridineHCID 11430Potassium CarbonateHCID 723356643-(2-chloro-6-trifluoromethyl-pyridin-3-yl)-N-(3-fluoro-4-methanesulfonylamino-benzyl)-acrylamide

Product 1

HCID 68783006HCID 68783006, compoundYield 82%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-(2-Chloro-6-trifluoromethyl-pyridin-3-yl)-N-(3-fluoro-4-methanesulfonylamino-benzyl)-acrylamide (48 mg, 0.11 mmol), 3-hydroxypyridine (97 mg) and potassium carbonate (421 mg) were added in 40 ml DMF. The reaction mixture was stirred overnight. The reaction mixture was extracted with ethyl acetate (30 ml×2) and water (30 ml). A combined organic layer was washed with H2O (30 ml×4) and brine (40 ml), dried with MgSO4, and then concentrated in vacuo. The residue was purified with column chromatography (hexane/ethylacetate=1/4) to yield the title compound (46 mg, 82%).

Workup

  1. extractionThe reaction mixture was extracted with ethyl acetate (30 ml×2) and water (30 ml)
  2. washA combined organic layer was washed with H2O (30 ml×4) and brine (40 ml)
  3. dry with materialdried with MgSO4
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified with column chromatography (hexane/ethylacetate=1/4)

Sources & evidence

ORD record
ord-3a25c88bcfbc4628885a1f6bc761d306
Source dataset
uspto-grants-2010_12
Patent number
US07858621B2

Reaction notes

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