3,5-Dimethyl-4-(tributylstannyl)isoxazole → 5-(3,5-dimethylisoxazol-4-yl)-1-(4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile

HRID 1410126Notes

Reaction equation

HRID 1410126 reaction equation
I[C:2]1[N:6]([C:7]2[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=2)[N:5]=[C:4]([CH3:15])[C:3]=1[C:16]#[N:17].[CH3:18][C:19]1[C:23]([Sn](CCCC)(CCCC)CCCC)=[C:22]([CH3:37])[O:21][N:20]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[CH3:18][C:19]1[C:23]([C:2]2[N:6]([C:7]3[CH:12]=[CH:11][C:10]([O:13][CH3:14])=[CH:9][CH:8]=3)[N:5]=[C:4]([CH3:15])[C:3]=2[C:16]#[N:17])=[C:22]([CH3:37])[O:21][N:20]=1

Participants

4

Reactant 2

HCID 150622153,5-Dimethyl-4-(tributylstannyl)isoxazoleHCID 671200735-iodo-1-(4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile

Product 1

HCID 671200255-(3,5-dimethylisoxazol-4-yl)-1-(4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrileYield 135.3%

Reagents, catalysts & solvents 1

HCID 178418476HCID 178418476, compoundCatalyst

Procedure

5-iodo-1-(4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (450 mg, 1.33 mmol), 3,5-dimethyl-4-(tributylstannyl)isoxazole (907 mg, 2.35 mmol) and PdCl2(PPh3)2 (186 mg, 0.27 mmol), were mixed with 1 mL degassed dioxane and 1 mL degassed DME under nitrogen in a microwave vial. The reaction was run at 145° C. in the microwave for 30 min. Water was added, extracted with CH2Cl2, filtered through a phase separator. The organic phase was evaporated and the residue was purified using silica to give 5-(3,5-dimethylisoxazol-4-yl)-1-(4-methoxyphenyl)-3-methyl-1H-pyrazole-4-carbonitrile (555 mg, >100%) which was used as such in the next step.

Workup

  1. customdegassed dioxane and 1 mL
  2. customdegassed DME under nitrogen in a microwave vial
  3. additionWater was added
  4. extractionextracted with CH2Cl2
  5. filtrationfiltered through a phase separator
  6. customThe organic phase was evaporated
  7. customthe residue was purified

Sources & evidence

ORD record
ord-dda3baac04194be3b49e6d492fe9c69f
Source dataset
uspto-grants-2014_12
Patent number
US08921402B2

Reaction notes

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