Triethylamine → methyl 5-chloro-4-(1-methyl-1H-1,2,3-triazol-5-yl)-2-thiophenecarboxylate

HRID 2392285Notes

Reaction equation

HRID 2392285 reaction equation
[CH3:1][N:2]1[C:6]([Sn](CCCC)(CCCC)CCCC)=[CH:5][N:4]=[N:3]1.Br[C:21]1[CH:22]=[C:23]([C:27]([O:29][CH3:30])=[O:28])[S:24][C:25]=1[Cl:26].C(N(CC)CC)C>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.C1(C)C=CC=CC=1>[Cl:26][C:25]1[S:24][C:23]([C:27]([O:29][CH3:30])=[O:28])=[CH:22][C:21]=1[C:6]1[N:2]([CH3:1])[N:3]=[N:4][CH:5]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 226098261-methyl-5-(tributylstannyl)-1H-1,2,3-triazoleHCID 57826388Methyl 4-bromo-5-chlorothiophene-2-carboxylate

Product 1

HCID 57826646methyl 5-chloro-4-(1-methyl-1H-1,2,3-triazol-5-yl)-2-thiophenecarboxylateYield 32%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 1-methyl-5-(tributylstannanyl)-1H-1,2,3-triazole (2.0 g, 5.37 mmol), methyl 4-bromo-5-chloro-2-thiophenecarboxylate (1.25 g, 4.9 mmol), Pd(PPh3)2Cl2 (171 mg, 0.244 mmol), TRIETHYLAMINE (0.68 ml, 4.89 mmol) and toluene (3 ml) was heated at 110° C. for 4 hr under N2. The reaction mixture was purified via column chromatography (silica, 50%-70% EtOAc in hexane) to give the title compound as a white solid (400 mg, 32%): LCMS (ES) m/z 258.2 (M+H)+.

Workup

  1. customThe reaction mixture was purified via column chromatography (silica, 50%-70% EtOAc in hexane)

Sources & evidence

ORD record
ord-71f26ab2cfd6422b95e03807d8a7f8c6
Source dataset
uspto-grants-2012_09
Patent number
US08273782B2

Reaction notes

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