HCID 23436208, compound → HCID 69892484, compound

HRID 2121266Notes

Reaction equation

HRID 2121266 reaction equation
[CH3:1][O:2][C:3](=[O:26])[C@H:4]([CH2:22][CH2:23][S:24][CH3:25])[NH:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10](I)=[CH:9][C:8]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20].[Cl:27][C:28]1[CH:33]=[CH:32][N:31]=[CH:30][C:29]=1[CH:34]=[CH2:35]>CN1C(=O)CCC1>[CH3:1][O:2][C:3](=[O:26])[C@H:4]([CH2:22][CH2:23][S:24][CH3:25])[NH:5][C:6](=[O:21])[C:7]1[CH:12]=[CH:11][C:10]([CH:35]=[CH:34][C:29]2[CH:30]=[N:31][CH:32]=[CH:33][C:28]=2[Cl:27])=[CH:9][C:8]=1[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][C:15]=1[CH3:20]

Participants

4

Reactant 2

HCID 23436208HCID 23436208, compoundHCID 69893156HCID 69893156, compound

Product 1

HCID 69892484HCID 69892484, compoundYield 46.5%

Reagents, catalysts & solvents 1

HCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

N-[4-iodo-2-(2-methylphenyl)benzoyl]methionine methyl ester (2.1 g, 4.34 mmol), 4-chloro-3-vinylpyridine (1.4 g, 10 mmol), and 1,1′-[bis(diphenylphosphino)ferrocene]dichloropalladium(II) (complex with methylene chloride 1:1, 177 mg, 0.22 mmol) were combined in NMP (9 mL) and TEA (3 mL) and heated at 100° C. for 5 hours. The mixture was concentrated and purified by flash chromatography (50% EtOAc in hexanes) to give 1.0 g of the title compound. MS m/e 495 (M+H)+. 1H NMR (CDCl3, 300 MHz) δ 1.61 (m, 2H), 1.90 (m, 2H), 2.15 (m, 6H), 3.69 (s, 3H), 4.65 (m, 1H), 5.95 (m, 1H), 7.3-7.5 (m, 9H), 7.69 (m, 1H), 8.05 (m, 1H), 8.45 (s, 1H).

Workup

  1. concentrationThe mixture was concentrated
  2. custompurified by flash chromatography (50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-81ef78f759524e508cc12a89f0e47ffd
Source dataset
uspto-grants-2004_02
Patent number
US06693123B2

Reaction notes

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