METHYL 3-AMINO-5-(4-METHYLPHENYL)THIOPHENE-2-CARBOXYLATE synthesis

8synthesis methods

Product Name:METHYL 3-AMINO-5-(4-METHYLPHENYL)THIOPHENE-2-CARBOXYLATE
CAS Number:37572-21-7
Molecular formula:C13H13NO2S
Molecular Weight:247.31

3-Amino-5-bromo-thiophene-2-carboxylic acid methyl ester

107818-55-3
85 suppliers
$27.00/100mg

5720-05-8
445 suppliers
$5.00/1g

METHYL 3-AMINO-5-(4-METHYLPHENYL)THIOPHENE-2-CARBOXYLATE

37572-21-7
12 suppliers
$104.00/1g

Yield:37572-21-7 89%

Reaction Conditions:

with palladium diacetate;sodium carbonate;triphenylphosphine in 1,4-dioxane;water at 80;Suzuki Coupling;

Steps:

General procedure for methyl 3-amino-5-arylthiophene-2-carboxylates (5)

General procedure: To a mixture of compound 4 (4.00-4.10 g,16.9-17.4 mmol) and arylboronic acid (1.1 M eq.) in 1,4-dioxane (80-85 mL) were added Pd(OAc)₂ (0.05 M eq.), triphenylphosphine (0.2 M eq.), and aqueous 0.53 N Na₂CO₃ (3 M eq.) solution at room temperature. The mixture was stirred at 80 °C for 3-3.5 h and cooled to room temperature. 1,4-Dioxane solvent was removed in vacuo and the residue was partitioned between DCM and brine. The organic layer was dried over MgSO₄ and concentrated in vacuo. The residue was chromatographed on a silica gel column with a mixture of n-hexane and ethyl acetate (3:1 for 5a; 6:1 for 5b-e) to give the desired product 5 (see Table 1 for yields).

References:

Ahn, Seohyeon;Jeon, Moon-Kook [Tetrahedron,2021,vol. 91,art. no. 132247]