Dimethylformamide → HCID 11538179, compound

HRID 732141Notes

Reaction equation

HRID 732141 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>CC(=O)OCC>[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-chloro-phenyl)-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 atm. 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 EA, sequentially washed with water and brine. The organic phase was dried (Na2SO4), filtered and concentrated, in-vacuo. The crude residue was purified via column chromatagraphy using 5% MeOH in EA 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. washsequentially washed with water and brine
  3. dry with materialThe organic phase was dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude residue was purified via column chromatagraphy

Sources & evidence

ORD record
ord-571ccf723ca7454b997c3b6486ad5289
Source dataset
uspto-grants-2009_09
Patent number
US07585881B2

Reaction notes

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