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

HRID 405179

反応式

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]

参加物

反応条件

温度: 100 °C

実験手順

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.

後処理

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

出典と根拠

ORDレコード: ord-8a53009bc9bd46ebb13421016b776abf
出典データセット: uspto-grants-2014_06
DOI: 10.6084/m9.figshare.5104873.v1
特許番号: US08748624B2

反応式

参加物

反応物 3

生成物 1

試薬・触媒・溶媒 2

反応条件

実験手順

後処理

出典と根拠

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