Water → HCID 71059956, compound

HRID 405226Notes

Reaction equation

HRID 405226 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:23][NH:24][C:25]2[CH:30]=[CH:29][C:28](I)=[CH:27][CH:26]=2)=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([NH:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[O:15])=[N:12][CH:13]=2)[CH:7]=1.[F:32][C:33]1[CH:38]=[CH:37][C:36](B(O)O)=[CH:35][C:34]=1[CH3:42].C([O-])([O-])=O.[K+].[K+].O>O1CCOCC1.C(Cl)Cl.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]>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([CH2:23][NH:24][C:25]2[CH:30]=[CH:29][C:28]([C:36]3[CH:37]=[CH:38][C:33]([F:32])=[C:34]([CH3:42])[CH:35]=3)=[CH:27][CH:26]=2)=[C:6]([C:8]2[CH:9]=[CH:10][C:11]([C:14]([NH:16][CH2:17][CH2:18][C:19]([O:21][CH3:22])=[O:20])=[O:15])=[N:12][CH:13]=2)[CH:7]=1

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 2774580(4-Fluoro-3-methylphenyl)boronic acidHCID 71059597HCID 71059597, compound

Product 1

HCID 71059956HCID 71059956, compound

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Procedure

Methyl 3-(5-(5-chloro-2-(((4-iodophenyl)amino)methyl)phenyl)picolinamido)propanoate (83 mg, 0.15 mmol), (4-fluoro-3-methylphenyl)boronic acid (31 mg, 0.20 mmol), Pd(dppf)Cl2 (12 mg, 0.02 mmol), and K2CO3 (55 mg, 0.40 mmol) were dissolved in 1,4-dioxane (1.5 mL) and water (0.5 mL) and heated to 90° C. After 1.5 h the resulting mixture was diluted with DCM, dried (Na2SO4), concentrated, and purified via column chromatography to yield the title compound.

Workup

  1. dry with materialdried (Na2SO4)
  2. concentrationconcentrated
  3. custompurified via column chromatography

Sources & evidence

ORD record
ord-c55162f4029b41e58fcf2a3d94aac2e2
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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