Water → 6-[3-(3-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-[1,2,4]triazolo[4,3-b]pyridazine

HRID 548892

Reaction equation

HRID 548892 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([CH2:13][OH:14])=[C:11]([CH3:15])[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1.[H-].[Na+].Cl[C:19]1[CH:20]=[CH:21][C:22]2[N:23]([CH:25]=[N:26][N:27]=2)[N:24]=1.O>CN(C=O)C>[F:1][C:2]1[CH:3]=[C:4]([C:8]2[C:12]([CH2:13][O:14][C:19]3[CH:20]=[CH:21][C:22]4[N:23]([CH:25]=[N:26][N:27]=4)[N:24]=3)=[C:11]([CH3:15])[O:10][N:9]=2)[CH:5]=[CH:6][CH:7]=1

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 3136246-Chloro-[1,2,4]triazolo[4,3-b]pyridazineHCID 67157856(3-(3-Fluorophenyl)-5-methylisoxazol-4-yl)methanol

Product 1

HCID 671580426-[3-(3-Fluoro-phenyl)-5-methyl-isoxazol-4-ylmethoxy]-[1,2,4]triazolo[4,3-b]pyridazineYield 51.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

To a solution of [3-(3-fluoro-phenyl)-5-methyl-isoxazol-4-yl]-methanol (100 mg, 0.48 mmol) in DMF (2 mL) was added sodium hydride (55% dispersion in mineral oil, 23.2 mg, 0.53 mmol). The mixture was stirred at room temperature for 15 min. After addition of a solution of 6-chloro-1,2,4-triazolo[4,3-b]pyridazine (82 mg, 0.53 mmol) in DMF (3 mL) the mixture was stirred at room temperature overnight. Then the mixture was poured into water, extracted (ethyl acetate/water) and the organic phase was dried with sodium sulfate and concentrated. Chromatography (SiO2, heptane:ethyl acetate=100:0 to 9:1) afforded the title compound (80 mg, 51%) as a white solid. MS: m/e=326.0 [M+H]+.

Workup

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

Sources & evidence

ORD record
ord-af8fc3c601894e38ac3ca4eff4f827ec
Source dataset
uspto-grants-2011_05
Patent number
US07943619B2

Linked notes

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