Sodium hydride → HCID 67157503, compound

HRID 548891Notes

Reaction equation

HRID 548891 reaction equation
[CH3:1][C:2]1[O:6][N:5]=[C:4]([C:7]2[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=2)[C:3]=1[CH2:13][OH:14].[H-].[Na+].Cl[C:18]1[CH:19]=[CH:20][C:21]2[N:22]([C:24]([C:27]3[O:28][CH:29]=[CH:30][CH:31]=3)=[N:25][N:26]=2)[N:23]=1>CN(C=O)C>[O:28]1[CH:29]=[CH:30][CH:31]=[C:27]1[C:24]1[N:22]2[N:23]=[C:18]([O:14][CH2:13][C:3]3[C:4]([C:7]4[CH:12]=[CH:11][CH:10]=[CH:9][CH:8]=4)=[N:5][O:6][C:2]=3[CH3:1])[CH:19]=[CH:20][C:21]2=[N:26][N:25]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 2776149(5-Methyl-3-phenyl-1,2-oxazol-4-yl)methanolHCID 21537475HCID 21537475, compound

Product 1

HCID 67157503HCID 67157503, compoundYield 87.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of (5-methyl-3-phenyl-isoxazol-4-yl)-methanol (60 mg, 0.32 mmol) in DMF (2 mL) was added sodium hydride (55% dispersion in mineral oil, 15 mg, 0.35 mmol). The mixture was stirred at room temperature overnight. After addition of a solution of 6-chloro-3-(2-furanyl)-1,2,4-triazolo[4,3-b]pyridazine (77 mg, 0.35 mmol) in DMF (2 mL) the mixture was stirred at room temperature overnight. Then the mixture was evaporated, extracted (ethyl acetate/water) and the organic phase was dried with sodium sulfate and concentrated. Chromatography (SiO2, heptane:ethyl acetate=100:0 to 1:1) afforded the title compound (105 mg, 67%) as a white foam. MS: m/e=374.5 [M+H]+.

Workup

  1. stirringwas stirred at room temperature overnight
  2. customThen the mixture was evaporated
  3. extractionextracted (ethyl acetate/water)
  4. dry with materialthe organic phase was dried with sodium sulfate
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-87c1fb4d52e645fda111708ac0140417
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Reaction notes

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