Pyridine → HCID 57641268, compound

HRID 2112292Notes

Reaction equation

HRID 2112292 reaction equation
[Cl:1][C:2]1[CH:7]=[C:6]([Cl:8])[CH:5]=[CH:4][C:3]=1[C:9]1[C:14]([CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])=[C:13]([CH3:24])[N:12]=[C:11]2[C:25](=[O:28])[NH:26][CH2:27][C:10]=12.[Cl:29][C:30]1[CH:35]=[CH:34][C:33](B(O)O)=[CH:32][CH:31]=1.CCN(CC)CC.N1C=CC=CC=1.ClC(Cl)C>CC([O-])=O.CC([O-])=O.[Cu+2]>[Cl:29][C:30]1[CH:35]=[CH:34][C:33]([N:26]2[CH2:27][C:10]3[C:11](=[N:12][C:13]([CH3:24])=[C:14]([CH2:15][NH:16][C:17](=[O:23])[O:18][C:19]([CH3:22])([CH3:21])[CH3:20])[C:9]=3[C:3]3[CH:4]=[CH:5][C:6]([Cl:8])=[CH:7][C:2]=3[Cl:1])[C:25]2=[O:28])=[CH:32][CH:31]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 63651,1-DichloroethaneHCID 8471TriethylamineHCID 742994-Chlorophenylboronic acidHCID 57641283HCID 57641283, compound

Product 1

HCID 57641268HCID 57641268, compoundYield 61%

Reagents, catalysts & solvents 1

HCID 8895Cupric acetateCatalyst

Procedure

A mixture of Example 11B (29.8 mg, 0.071 mmol), 4-chlorophenylboronic acid (45 mg, 0.288 mmol), Cu(OAc)2 (24 mg, 0.132 mmol), Et3N (45 μL, 0.324 mmol), pyridine (60 μL, 0.743 mmol), and dichloroethane (1 mL) was heated at 75° C. for 1.5 h. Concentration in vacuo followed by flash chromatography (50% to 100% EtOAc/Hexanes) to yield a Example 11C which was further purified by recrystallization fom MeOH to give 23 mg (61%) of a solid.

Workup

  1. concentrationConcentration in vacuo
  2. customto yield a Example 11C which
  3. customwas further purified by recrystallization fom MeOH

Sources & evidence

ORD record
ord-963690d5864a4ac3bf85a0b6634ecf18
Source dataset
uspto-grants-2009_04
Patent number
US07521557B2

Reaction notes

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