Potassium Phosphate, Tribasic → Ethyl 3-(5-(2-formyl-6-(trifluoromethyl)phenyl)picolinamido)propanoate

HRID 405179

Reaction equation

Cl[C:2]1[C:9]([C:10]([F:13])([F:12])[F:11])=[CH:8][CH:7]=[CH:6][C:3]=1[CH:4]=[O:5].CC1(C)C(C)(C)OB([C:22]2[CH:23]=[CH:24][C:25]([C:28]([NH:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:29])=[N:26][CH:27]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH:4]([C:3]1[CH:6]=[CH:7][CH:8]=[C:9]([C:10]([F:13])([F:12])[F:11])[C:2]=1[C:22]1[CH:23]=[CH:24][C:25]([C:28]([NH:30][CH2:31][CH2:32][C:33]([O:35][CH2:36][CH3:37])=[O:34])=[O:29])=[N:26][CH:27]=1)=[O:5]

Participants

Conditions

Temperature: 100 °C

Procedure

2-Chloro-3-(trifluoromethyl)benzaldehyde (199 mg, 0.96 mmol), ethyl 3-(5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)picolinamido)propanoate (410 mg, 1.2 mmol), Pd2(dba)3 (26 mg, 0.03 mmol), and 2M K3PO4 (aq) (1.0 mL, 2.0 mmol) were dissolved in 1,4-dioxane (2.9 mL) and heated to 100° C. After 2.5 h the resulting mixture was concentrated, taken up in DCM and the aqueous layer was extracted with DCM. The combined organics were dried (Na2SO4), concentrated and purified via column chromatography to yield the title compound.

Workup

concentrationAfter 2.5 h the resulting mixture was concentrated
extractionthe aqueous layer was extracted with DCM
dry with materialThe combined organics were dried (Na2SO4)
concentrationconcentrated
custompurified via column chromatography

Sources & evidence

ORD record: ord-8a53009bc9bd46ebb13421016b776abf
Source dataset: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08748624B2

Linked notes

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