Water → Ethyl 3-(5-(5-methoxy-2-(((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate

HRID 405166Notes

Reaction equation

HRID 405166 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][C:13]([O:16][CH3:17])=[CH:12][C:11]=2[C:18]2[CH:19]=[CH:20][C:21]([C:24]([NH:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:25])=[N:22][CH:23]=2)=[CH:4][CH:3]=1.[F:34][C:35]([F:46])([F:45])[C:36]1[CH:41]=[CH:40][C:39](B(O)O)=[CH:38][CH:37]=1.C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.CCOC(C)=O.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]>[CH3:17][O:16][C:13]1[CH:14]=[CH:15][C:10]([CH2:9][NH:8][C:5]2[CH:6]=[CH:7][C:2]([C:39]3[CH:40]=[CH:41][C:36]([C:35]([F:46])([F:45])[F:34])=[CH:37][CH:38]=3)=[CH:3][CH:4]=2)=[C:11]([C:18]2[CH:19]=[CH:20][C:21]([C:24]([NH:26][CH2:27][CH2:28][C:29]([O:31][CH2:32][CH3:33])=[O:30])=[O:25])=[N:22][CH:23]=2)[CH:12]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343894-(Trifluoromethyl)phenylboronic acidHCID 71060028Ethyl 3-(5-(2-(((4-bromophenyl)amino)methyl)-5-methoxyphenyl)picolinamido)propanoate

Product 1

HCID 71059803Ethyl 3-(5-(5-methoxy-2-(((4'-(trifluoromethyl)-[1,1'-biphenyl]-4-yl)amino)methyl)phenyl)picolinamido)propanoate

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8857Ethyl AcetateSolventHCID 312751,4-DioxaneSolvent

Procedure

Ethyl 3-(5-(2-(((4-bromophenyl)amino)methyl)-5-methoxyphenyl)picolinamido)propanoate (200 mg, 0.39 mmol), (4-(trifluoromethyl)phenyl)boronic acid (111 mg, 0.59 mmol), Pd(dppf)Cl2 (43 mg, 0.06 mmol), and K2CO3 (108 mg, 0.78 mmol) were dissolved in 1,4-dioxane (4 mL) and water (1 mL) and the resulting mixture was heated to 80° C. After 2 h the resulting mixture was cooled to room temperature, diluted with EtOAc, washed with water and brine, dried (Na2SO4), and dry packed onto silica gel. Column chromatography yielded the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customdry

Sources & evidence

ORD record
ord-d93880c79df942cfa41e0a301ef9d8b8
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

Loading…