Water → HCID 71060082, compound

HRID 405126Notes

Reaction equation

HRID 405126 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([NH:8][CH2:9][C:10]2[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=2[C:16]2[CH:17]=[CH:18][C:19]([C:22]([NH:24][CH2:25][CH2:26][C:27]([O:29][C:30]([CH3:33])([CH3:32])[CH3:31])=[O:28])=[O:23])=[N:20][CH:21]=2)=[CH:4][CH:3]=1.[Cl:34][C:35]1[CH:36]=[C:37](B(O)O)[CH:38]=[CH:39][C:40]=1[Cl:41].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]>[Cl:34][C:35]1[CH:36]=[C:37]([C:2]2[CH:3]=[CH:4][C:5]([NH:8][CH2:9][C:10]3[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=3[C:16]3[CH:17]=[CH:18][C:19]([C:22]([NH:24][CH2:25][CH2:26][C:27]([O:29][C:30]([CH3:32])([CH3:31])[CH3:33])=[O:28])=[O:23])=[N:20][CH:21]=3)=[CH:6][CH:7]=2)[CH:38]=[CH:39][C:40]=1[Cl:41]

Participants

8

Reactant 4

HCID 962WaterHCID 11430Potassium CarbonateHCID 27343303,4-Dichlorobenzeneboronic acidHCID 71059974HCID 71059974, compound

Product 1

HCID 71060082HCID 71060082, compound

Reagents, catalysts & solvents 3

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

Procedure

tert-butyl 3-(5-(2-(((4-bromophenyl)amino)methyl)phenyl)picolinamido)propanoate (80 mg, 0.16 mmol), (3,4-dichlorophenyl)boronic acid (34 mg, 0.18 mmol), Pd(dppf)Cl2 (13 mg, 0.02 mmol), and K2CO3 (43 mg, 0.31 mmol) were dissolved in 1,4-dioxane (1.2 mL) and water (0.3 mL) and heated to 80° C. After 3 h the resulting mixture was cooled to room temperature, diluted with EtOAc washed with water and brine, dried (Na2SO4), dry-packed onto silica gel and purified via column chromatography to yield the title compound.

Workup

  1. washwashed with water and brine
  2. dry with materialdried (Na2SO4)
  3. customdry-packed onto silica gel and purified via column chromatography

Sources & evidence

ORD record
ord-f113f8437f8d4a6c800a84344154aede
Source dataset
uspto-grants-2014_06
Patent number
US08748624B2

Reaction notes

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