Water → 4-methyl-2-[6-((E)-3-phenyl-propenyl)-pyrazin-2-yl]-thiazole-5-carboxylic acid benzylamide

HRID 1879142Notes

Reaction equation

HRID 1879142 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[CH:21]=[N:20][CH:19]=[C:18](I)[N:17]=2)=[N:13][C:12]=1[CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[C:30]1([CH2:36]/[CH:37]=[CH:38]/B(O)O)[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=1.O>COC.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]>[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14]([C:16]2[CH:21]=[N:20][CH:19]=[C:18](/[CH:38]=[CH:37]/[CH2:36][C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[N:17]=2)=[N:13][C:12]=1[CH3:23])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 11041016trans-3-Phenylpropen-1-yl-boronic acidHCID 732132692-(6-Iodo-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid benzylamide

Product 1

HCID 684877744-methyl-2-[6-((E)-3-phenyl-propenyl)-pyrazin-2-yl]-thiazole-5-carboxylic acid benzylamideYield 50.8%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 8254Dimethyl EtherSolvent

Procedure

Part A. To a solution of 2-(6-iodo-pyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid benzylamide (80 mg, 0.18 mmol, 1.0 equiv) in dimethyl ether (1 mL) was added Na2CO3 (38 mg, 0.36 mmol, 2.0 equiv), trans-3-phenylpropen-1-yl boronic acid (73 mg, 0.45 mmol, 2.5 equiv), PdCl2(dppf) (1.3 mg, 0.02 mmol, 0.1 equiv) and water (0.1 mL) in a sealed tube. The reaction vessel was immersed in an oil bath preheated to 60° C. After stirring for 3 hr, the reaction mixture was cooled and the solvent was removed in vacuo. The crude product was purified by column chromatography [SiO2, methanol/dichloromethane, 0:100 to 10:90, v/v] to give 4-methyl-2-[6-((E)-3-phenyl-propenyl)-pyrazin-2-yl]-thiazole-5-carboxylic acid benzylamide (39 mg, 50%); MS (M+H)+=427.1, Rt=1.70 min.

Workup

  1. customThe reaction vessel was immersed in an oil bath
  2. custompreheated to 60° C
  3. temperaturethe reaction mixture was cooled
  4. customthe solvent was removed in vacuo
  5. customThe crude product was purified by column chromatography [SiO2, methanol/dichloromethane, 0:100 to 10:90

Sources & evidence

ORD record
ord-40f53bfb8c054b69a442c32dfd5141b9
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

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