4-Vinylpyridine → HCID 69913671, compound

HRID 431370Notes

Reaction equation

HRID 431370 reaction equation
[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12](Br)[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1.[CH:16]([C:18]1[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=1)=[CH2:17].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>CCN(CC)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][O:2][C:3](=[O:15])[C:4]1[CH:13]=[C:12]([CH:17]=[CH:16][C:18]2[CH:23]=[CH:22][N:21]=[CH:20][CH:19]=2)[CH:11]=[C:6]([C:7]([O:9][CH3:10])=[O:8])[CH:5]=1

Participants

6

Reactant 3

HCID 75024-VinylpyridineHCID 80271Tri-o-tolylphosphineHCID 1039541,3-Benzenedicarboxylic acid, 5-bromo-, 1,3-dimethyl ester

Product 1

HCID 69913671HCID 69913671, compoundYield 65%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 8471TriethylamineSolvent

Procedure

A solution of 5-bromoisophthalic acid dimethylester (542 mg, 2 mmol) and 4-vinylpyridine (206 mg, 2 mmol), Pd(OAc)2 (8 mg), tri-o-tolylphosphine (30 mg) in 5 ml Et3N (5 ml) was stirred at 80° C. for overnight. The reaction mixture was purified by silica gel column eluted by 50% EtOAc in hexane to afford the product (65% yield). MS+=297. 1H NMR (CDCl3, 400 MHz) 8.64 (s, 1H), 8.61 (d, 2H), 8.38 (d, 2H), 7.40 (m, 2H), 7.35 (m, 1H), 7.21 (m, 1H), 4.02 (s, 6H);

Workup

  1. customThe reaction mixture was purified by silica gel column
  2. washeluted by 50% EtOAc in hexane

Sources & evidence

ORD record
ord-202484aabdca49b7b9fc1879f4ee675c
Source dataset
uspto-grants-2003_12
Patent number
US06656971B2

Reaction notes

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