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Potassium Phosphate, Tribasic → Ethyl 3-(5-(2-formyl-3-methoxy-5-(trifluoromethyl)phenyl)picolinamido)propanoate

HRID 405245
Notes
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Reaction equation

HRID 405245 reaction equation
Cl[C:2]1[CH:9]=[C:8]([C:10]([F:13])([F:12])[F:11])[CH:7]=[C:6]([O:14][CH3:15])[C:3]=1[CH:4]=[O:5].CC1(C)C(C)(C)OB([C:24]2[CH:25]=[CH:26][C:27]([C:30]([NH:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:31])=[N:28][CH:29]=2)O1.COC1C=CC=C(OC)C=1C1C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.O.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH:4]([C:3]1[C:6]([O:14][CH3:15])=[CH:7][C:8]([C:10]([F:13])([F:12])[F:11])=[CH:9][C:2]=1[C:24]1[CH:25]=[CH:26][C:27]([C:30]([NH:32][CH2:33][CH2:34][C:35]([O:37][CH2:38][CH3:39])=[O:36])=[O:31])=[N:28][CH:29]=1)=[O:5]
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 112698722-Dicyclohexylphosphino-2',6'-dimethoxybiphenylHCID 71059832Ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoateHCID 840702922-Chloro-6-methoxy-4-(trifluoromethyl)benzaldehyde

Product 1

HCID 86674280
Ethyl 3-(5-(2-formyl-3-methoxy-5-(trifluoromethyl)phenyl)picolinamido)propanoate

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolventHCID 1140TolueneSolvent

Conditions

Temperature
90 °C

Procedure

2-Chloro-6-methoxy-4-(trifluoromethyl)benzaldehyde (272.1 mg, 1.14 mmol), ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate (516.2 mg, 1.48 mmol), SPhos (140.5 mg, 0.34 mmol), Pd(OAc)2 (38.4 mg, 0.17 mmol) and K3PO4 (726.3 mg, 3.42 mmol) were dissolved in wet PhMe (8 mL) and the resulting mixture was heated to 90° C. After 16 h the resulting mixture was diluted with water and extracted with EtOAc. The combined organic extracts were dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Workup

  1. extractionextracted with EtOAc
  2. dry with materialThe combined organic extracts were dried (Na2SO4)
  3. concentrationconcentrated
  4. custompurified via column chromatography

Sources & evidence

ORD record
ord-e9e23e8e5a624fc0b6b4243ad3bff7e7
Source dataset
uspto-grants-2014_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08748624B2

Reaction notes

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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes