Dimethylformamide → HCID 11538179, compound

HRID 1453809Notes

Reaction equation

HRID 1453809 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH:13]([OH:15])[CH3:14])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1.CN(C=O)C.[H-].[Na+].[CH3:23][N:24]1[C:28](S(C)(=O)=O)=[N:27][N:26]=[C:25]1[C:33]1[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=1>CCOC(C)=O>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]2[O:12][N:11]=[C:10]([CH:13]([O:15][C:28]3[N:24]([CH3:23])[C:25]([C:33]4[CH:38]=[CH:37][N:36]=[CH:35][CH:34]=4)=[N:26][N:27]=3)[CH3:14])[CH:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 6228DimethylformamideHCID 24758Sodium hydrideHCID 221514774-[5-(Methanesulfonyl)-4-methyl-4H-1,2,4-triazol-3-yl]pyridineHCID 57528604HCID 57528604, compound

Product 1

HCID 11538179HCID 11538179, compoundYield 16.1%

Reagents, catalysts & solvents 1

HCID 8857Ethyl AcetateSolvent

Procedure

1-[5-(3-chlorophenyl)isoxazol-3-yl]ethanol (63.4 mg, 0.28 mmol), DMF and sodium hydride (60% dispersion in oil, 15.1 mg, 0.38 mmol) were mixed under inert atmosphere and stirred at r.t for 1 h, followed by addition of 4-[4-methyl-5-(methylsulfonyl)-4H-1,2,4-triazol-3-yl]pyridine (45 mg, 0.19 mmol). After stirring at 80° C. for 24 h, the mixture was cooled to r.t., diluted with EtOAc and washed with water and brine. The organic phase was dried (Na2SO4), filtered and concentrated in vacuo. The crude residue was purified via column chromatography on silica using 5% methanol in EtOAc to isolate the title compound (11.7 mg). 1H-NMR: 8.81 (bs, 2H), 7.77 (s, 1H), 7.67 (m, 3H), 7.42 (m, 2H), 6.73 (s, 1H), 6.36 (q, 1H), 3.62 (s, 3H), 1.94 (d, 3H).

Workup

  1. stirringAfter stirring at 80° C. for 24 h
  2. washwashed with water and brine
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude residue was purified via column chromatography on silica using 5% methanol in EtOAc

Sources & evidence

ORD record
ord-635fa53449bc406695a0bc5ae0192fca
Source dataset
uspto-grants-2009_01
Patent number
US07476684B2

Reaction notes

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