Dimethylformamide → HCID 67778475, compound

HRID 1026276Notes

Reaction equation

HRID 1026276 reaction equation
[CH2:1]([N:8]1[C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11](Br)[C:10]([O:18][CH2:19][C@@H:20]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH3:21])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:30]B1OB(C)OB(C)O1.C(=O)([O-])[O-].[K+].[K+].CN(C=O)C>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].ClCCl.O>[CH2:1]([N:8]1[C:12]([C:13]([O:15][CH3:16])=[O:14])=[C:11]([CH3:30])[C:10]([O:18][CH2:19][C@@H:20]([NH:22][C:23]([O:25][C:26]([CH3:29])([CH3:28])[CH3:27])=[O:24])[CH3:21])=[N:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 6228DimethylformamideHCID 11430Potassium CarbonateHCID 574072TrimethylboroxineHCID 67777572HCID 67777572, compound

Product 1

HCID 67778475HCID 67778475, compoundYield 37.2%

Reagents, catalysts & solvents 2

HCID 178418807HCID 178418807, compoundCatalystHCID 962WaterSolvent

Conditions

Temperature
155 °C

Procedure

Under an argon atmosphere, a mixture of methyl 1-benzyl-4-bromo-3-({(2S)-2-[(tert-butoxycarbonyl)amino]propyl}oxy)-1H-pyrazole-5-carboxylate (1.03 g), trimethylboroxin (552 mg), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane adduct (181 mg), potassium carbonate (912 mg) and DMF (20 ml) was stirred at 155° C. overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained organic layer was washed with saturated brine, and dried over anhydrous magnesium sulfate, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (hexane/ethyl acetate) to give the title compound as a white powder (330 mg).

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe obtained organic layer was washed with saturated brine
  3. dry with materialdried over anhydrous magnesium sulfate
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (hexane/ethyl acetate)

Sources & evidence

ORD record
ord-16f2d1fe51f24173ad7e22c35a97d7af
Source dataset
uspto-grants-2014_05
Patent number
US08729102B2

Reaction notes

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