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Potassium Phosphate, Tribasic → HCID 86721254, compound

HRID 1750409
Notes
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Reaction equation

HRID 1750409 reaction equation
Br[C:2]1[N:6]([C:7]([CH3:10])([CH3:9])[CH3:8])[N:5]=[CH:4][C:3]=1[C:11]([NH2:13])=[O:12].[CH3:14][O:15][C:16]1[CH:21]=[CH:20][C:19](/[CH:22]=[CH:23]/B(O)O)=[CH:18][CH:17]=1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1COCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[C:7]([N:6]1[C:2](/[CH:23]=[CH:22]/[C:19]2[CH:20]=[CH:21][C:16]([O:15][CH3:14])=[CH:17][CH:18]=2)=[C:3]([C:11]([NH2:13])=[O:12])[CH:4]=[N:5]1)([CH3:10])([CH3:9])[CH3:8]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 642693trans-2-(4-Methoxyphenyl)vinylboronic acidHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 86721240HCID 86721240, compound

Product 1

HCID 86721254HCID 86721254, compoundYield 16.4%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalyst
HCID 962WaterSolvent
HCID 8028TetrahydrofuranSolvent

Procedure

A solution of 5-bromo-1-tert-butyl-1H-pyrazole-4-carboxamide (100 mg, 0.41 mmol), trans-2-(4-methoxyphenyl)vinylboronic acid (108 mg, 0.61 mmol), S-phos (3.34 mg, 8.13 μmol), palladium(II) acetate (0.912 mg, 4.06 μmol) and tripotassium phosphate (173 mg, 0.81 mmol) in THF (2 mL) was stirred under an argon atmosphere at 40° C. for 14 hr. Water was added to the reaction solution, and the mixture was extracted with ethyl acetate. The organic layer was washed with saturated brine and dried, and the solvent was evaporated under reduced pressure. The residue was purified by silica gel column chromatography (solvent gradient; 3→100% ethyl acetate/hexane) to give (E)-1-tert-butyl-5-(4-methoxystyryl)-1H-pyrazole-4-carboxamide (20 mg, 0.067 mmol, 16.4%) as a white powder.

Workup

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with saturated brine
  3. customdried
  4. customthe solvent was evaporated under reduced pressure
  5. customThe residue was purified by silica gel column chromatography (solvent gradient; 3→100% ethyl acetate/hexane)

Sources & evidence

ORD record
ord-324c950f3e854dfa977fb0e20a2558e9
Source dataset
uspto-grants-2015_10
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09156837B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes