Water → HCID 24954330, compound

HRID 1879137Notes

Reaction equation

HRID 1879137 reaction equation
[CH2:1]([NH:8][C:9]([C:11]1[S:15][C:14](Br)=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])([O-])=O.[Na+].[Na+].[Cl:24][C:25]1[N:30]=[C:29](B2OC(C)(C)C(C)(C)O2)[CH:28]=[N:27][CH:26]=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:29]2[CH:28]=[N:27][CH:26]=[C:25]([Cl:24])[N:30]=2)=[N:13][C:12]=1[CH3:17])=[O:10])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 177504862-Chloro-6-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyrazineHCID 579593962-Bromo-4-methyl-thiazole-5-carboxylic acid benzylamide

Product 1

HCID 24954330HCID 24954330, compoundYield 23.1%

Reagents, catalysts & solvents 2

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

Procedure

Part B. To a solution of 2-bromo-4-methyl-thiazole-5-carboxylic acid benzylamide (350 mg, 1.13 mmol, 1.0 equiv) in dimethyl ether (4 mL) was added Na2CO3 (240 mg, 2.26 mmol, 2.0 equiv), 6-chloropyrazine-2-boronic acid pinacol ester (680 mg, 2.82 mmol, 2.5 equiv), PdCl2(dppf) (83 mg, 0.11 mmol, 0.1 equiv) and water (1 mL) in a sealed tube. The reaction was immersed in an oil bath preheated to 50° C. After 3 days, the reaction was cooled and the solvent was removed in vacuo. The crude product was purified by preparative HPLC (acetonitrile/water, 0.1% trifluoroacetic acid) to give 2-(6-chloropyrazin-2-yl)-4-methyl-thiazole-5-carboxylic acid benzylamide (90 mg, 23% yield). 1H NMR (400 MHz, DMSO-d6) δ 9.27 (s, 1H), 8.93 (s, 1H), 7.31-7.39 (m, 4H), 7.23-7.30 (m, 1H), 4.46 (d, J=8.0 Hz, 2H), 2.67 (s, 3H); MS (M+H)+=345.1, Rt=1.46 min.

Workup

  1. customThe reaction was immersed in an oil bath
  2. custompreheated to 50° C
  3. temperaturethe reaction was cooled
  4. customthe solvent was removed in vacuo
  5. customThe crude product was purified by preparative HPLC (acetonitrile/water, 0.1% trifluoroacetic acid)

Sources & evidence

ORD record
ord-2a958f1d03634b57a6ff64943905d3fa
Source dataset
uspto-grants-2012_11
Patent number
US08314138B2

Reaction notes

Loading…