Triethylamine → HCID 68528893, compound

HRID 1932473Notes

Reaction equation

HRID 1932473 reaction equation
C(N(CC)CC)C.[NH2:8][C:9]1[CH:10]=[CH:11][C:12]([O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:18][CH:17]=2)=[N:13][CH:14]=1.[Cl:29][C:30]1[CH:31]=[C:32](B(O)O)[CH:33]=[CH:34][C:35]=1[Cl:36]>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[Cl:29][C:30]1[CH:31]=[C:32]([NH:8][C:9]2[CH:10]=[CH:11][C:12]([O:15][C:16]3[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:18][CH:17]=3)=[N:13][CH:14]=2)[CH:33]=[CH:34][C:35]=1[Cl:36]

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27343303,4-Dichlorobenzeneboronic acidHCID 68528473HCID 68528473, compound

Product 1

HCID 68528893HCID 68528893, compound

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Triethylamine (1.2 mL, 8.4 mmol) was added to a suspension of ethyl 3-(4-(5-aminopyridin-2-yloxy)phenyl)propionate (1.2 g, 4.2 mmol), 3,4-dichlorophenylboronic acid (1.6 g, 8.4 mmol), anhydrous copper acetate (0.762 g, 4.2 mmol) and molecular sieves 4A (5 g) in dichloromethane (24 mL), and the resulting reaction solution was stirred overnight at room temperature. After the resulting solution was filtered through Celite, the filtrate was concentrated under reduced pressure. The residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1), to thereby yield 1.5 g of the title compound.

Workup

  1. customthe resulting reaction solution
  2. filtrationAfter the resulting solution was filtered through Celite
  3. concentrationthe filtrate was concentrated under reduced pressure
  4. customThe residue was purified by silica gel chromatography (n-hexane:ethyl acetate=4:1)

Sources & evidence

ORD record
ord-19675c0108d448ce914b4a1be1d294e7
Source dataset
uspto-grants-2012_05
Patent number
US08188277B2

Reaction notes

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