1,4-Dioxane → HCID 123172170, compound

HRID 1773692Notes

Reaction equation

HRID 1773692 reaction equation
Br[C:2]1[N:6]([CH3:7])[N:5]=[CH:4][C:3]=1[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.CC1C([B:20]2[O:28][C:25]([CH3:27])([CH3:26])[C:22]([CH3:24])([CH3:23])[O:21]2)=C(C)ON=1.O1CCOCC1.C([O-])(=O)C.[K+]>CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[CH3:7][N:6]1[C:2]([B:20]2[O:28][C:25]([CH3:27])([CH3:26])[C:22]([CH3:24])([CH3:23])[O:21]2)=[C:3]([C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:4]=[N:5]1

Participants

7

Reactant 4

HCID 312751,4-DioxaneHCID 517044Potassium AcetateHCID 27586563,5-Dimethylisoxazole-4-boronic acid pinacol esterHCID 83382776HCID 83382776, compound

Product 1

HCID 123172170HCID 123172170, compoundYield 134.1%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
100 °C

Procedure

5-bromo-1-methyl-4-phenyl-1H-pyrazole (87 mg, 0.37 mmol) and 3,5-Dimethylisoxazole-4-boronic acid pinacol ester (373 mg, 1.47 mmol) was added to a 1,4-dioxane (2 ml). To the above mixture were added Pd(dppf)Cl2 (27 mg, 0.037 mmol) and potassium acetate (181 mg, 1.85 mmol). The reaction mixture was heated at 100° C. for 2 h. The reaction mixture was then diluted with EtOAc (100 ml), washed with bring (50 ml×2). The organic solvent was evaporated and the residue was dissolved in DCM and purified with combi-flash column chromatography (product came out at 45% EtOAc/Hexane) to afford 141 mg product 1-methyl-4-phenyl-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole.

Workup

  1. washwashed
  2. customThe organic solvent was evaporated
  3. dissolutionthe residue was dissolved in DCM
  4. custompurified with combi-flash column chromatography (product

Sources & evidence

ORD record
ord-77d7905b1d1346968e2765f21546c72a
Source dataset
uspto-grants-2016_02
Patent number
US09255089B2

Reaction notes

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