6H-Thieno[2,3-b]pyrrole-4-acetamide synthesis

Yield:842165-39-3 100%

Reaction Conditions:

Stage #1: with trimethylaluminum;ammonium chloride in toluene at 5 - 20; for 2 h;
Stage #2: ethyl (6-H-4-tieno<2,3-b>pyrrolyl)acetate in toluene at 50; for 16 h;

Steps:

5

EXAMPLE 5 Preparation of 1- (THIENOR2, 3-BLPVRROL-4-VL) acetamide A stirred suspension of ammonium chloride (963 mg, 3 equiv. ) in toluene at 5°C is treated with TRIMETHYLALUMINUM (9 mL of 2 M solution in toluene, 3 equiv.), stirred at room temperature for 2 h, treated with a solution of ethyl 1- (THIENO [2,3- b] pyrrol-4-yl) acetate (1.25 g, 6 MMOL, 1 equiv. ) in toluene, heated at 50°C for 16 h, cooled to room temperature, quenched with water and extracted with EtOAc. The extracts are combined, dried over MGS04 and CONCENTRATED IN VACUO TO give the title product as a tan oil, 1. 1g (quantitative yield), identified by liquid chromatography and mass spectral analyses.

References:

WO2005/12311,2005,A1 Location in patent:Page/Page column 24