Dimethylformamide → HCID 86684858, compound

HRID 238356Notes

Reaction equation

HRID 238356 reaction equation
FC(F)(F)S(O[C:7]1[CH:12]=[CH:11][C:10]([C:13]2[N:17]([CH3:18])[N:16]=[CH:15][CH:14]=2)=[CH:9][CH:8]=1)(=O)=O.[N:21]1[CH:26]=[CH:25][CH:24]=[C:23](B(O)O)[CH:22]=1.C(=O)([O-])[O-].[K+].[K+].CN(C)C=O>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.O.C(O)C>[CH3:18][N:17]1[C:13]([C:10]2[CH:11]=[CH:12][C:7]([C:23]3[CH:22]=[N:21][CH:26]=[CH:25][CH:24]=3)=[CH:8][CH:9]=2)=[CH:14][CH:15]=[N:16]1

Participants

8

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 27343783-Pyridinylboronic acidHCID 86684859HCID 86684859, compound

Product 1

HCID 86684858HCID 86684858, compoundYield 143.2%

Reagents, catalysts & solvents 3

HCID 178418476HCID 178418476, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolvent

Procedure

A mixture of 4-(1-methyl-1H-pyrazol-5-yl)phenyl trifluoromethanesulfonate (200 mg), 3-pyridylboronic acid (88 mg), bis(triphenylphosphine)palladium(II) dichloride (14 mg), potassium carbonate (135 mg), dimethylformamide (1.4 mL) and ethanol (0.70 mL) was reacted in a microwave reactor (80° C., 25 minutes). Thereafter, water was added to the reaction solution, and the obtained mixture was extracted with ethyl acetate. The organic layer was washed with water and a saturated saline, and was then dried over anhydrous magnesium sulfate, followed by vacuum concentration, so as to obtain the title compound (220 mg) in the form of a light yellow oily substance.

Workup

  1. customwas reacted in a microwave reactor (80° C., 25 minutes)
  2. extractionthe obtained mixture was extracted with ethyl acetate
  3. washThe organic layer was washed with water
  4. dry with materiala saturated saline, and was then dried over anhydrous magnesium sulfate
  5. concentrationfollowed by vacuum concentration

Sources & evidence

ORD record
ord-0f255a4b4d6540c38f196799fffa10f6
Source dataset
uspto-grants-2014_02
Patent number
US08642626B2

Reaction notes

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