Sodium Carbonate → Ethyl 2-(2-methoxyphenyl)-1,3-thiazole-4-carboxylate

HRID 460186Notes

Reaction equation

HRID 460186 reaction equation
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1B(O)O.Br[C:13]1[S:14][CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=1.C([O-])([O-])=O.[Na+].[Na+]>COCCOC.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]>[CH3:1][O:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:13]1[S:14][CH:15]=[C:16]([C:18]([O:20][CH2:21][CH3:22])=[O:19])[N:17]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 353965Ethyl 2-bromo-1,3-thiazole-4-carboxylateHCID 27339582-Methoxyphenylboronic acid

Product 1

HCID 10015624Ethyl 2-(2-methoxyphenyl)-1,3-thiazole-4-carboxylate

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 80711,2-DimethoxyethaneSolvent

Procedure

A suspension of 2-methoxyphenyl boronic acid (0.25 g, 1.65 mmol), ethyl 2-bromothiazole-4-carboxylate (0.33 g, 1.4 mmol), PdCl2(dppf)2 (0.11 g, 0.14 mmol) and 2M Na2CO3(aq) (2 mL) in DME (10 mL) was heated at reflux for 20 h, cooled to RT, filtered, concentrated by rotary evaporation and purified on silica gel (6:1 hexanes/EtOAc and 4:1 hexanes/EtOAc) to afford the title compound as a light-brown oil. EI-MS m/z 264 (M+H).

Workup

  1. temperaturewas heated
  2. temperatureat reflux for 20 h
  3. filtrationfiltered
  4. concentrationconcentrated by rotary evaporation
  5. custompurified on silica gel (6:1 hexanes/EtOAc and 4:1 hexanes/EtOAc)

Sources & evidence

ORD record
ord-6368c9f9dfd4423097c10d98956241d3
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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