Cesium carbonate → 4-Methyl-5-naphthalen-1-yl-thiazole-2-carboxylic acid ethyl ester

HRID 12452

Reaction equation

HRID 12452 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8](Br)=[C:9]([CH3:11])[N:10]=1)=[O:5])[CH3:2].[C:13]1(B(O)O)[C:22]2[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=2)[CH:16]=[CH:15][CH:14]=1.C(=O)([O-])[O-].[Cs+].[Cs+]>O1CCOCC1.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[CH2:1]([O:3][C:4]([C:6]1[S:7][C:8]([C:21]2[C:22]3[C:17](=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:18]=[CH:19][CH:20]=2)=[C:9]([CH3:11])[N:10]=1)=[O:5])[CH3:2]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 2545321-Naphthaleneboronic acidHCID 59338079Ethyl 5-bromo-4-methylthiazole-2-carboxylate

Product 1

HCID 593384494-Methyl-5-naphthalen-1-yl-thiazole-2-carboxylic acid ethyl ester

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

To a solution of 5-bromo-4-methyl-thiazole-2-carboxylic acid ethyl ester (60 mg, 0.24 mmol) in 1,4-dioxane (2 ml) is added 1-naphthaleneboronic acid (50 mg, 0.29 mmol), cesium carbonate (187 mg, 0.58 mmol) and Pd(PPh3)4 (28 mg, 0.024 mmol). The reaction mixture is stirred in a sealed tube at 110° C. overnight. After cooling to rt, the mixture is purified by PTLC to give the title compound.

Workup

  1. temperatureAfter cooling to rt
  2. customthe mixture is purified by PTLC

Sources & evidence

ORD record
ord-9f1c3eae5e914686a5941e976dd60d69
Source dataset
uspto-grants-2010_06
Patent number
US07728009B1

Linked notes

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