Reaction #1441915

Reaction equation

5-Bromofuran-2-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide

1-butoxy-4-ethynylbenzene

N,N-diisopropylamine

→

5-(4-Butoxyphenylethynyl)furan-2-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)-phenyl]amide

Solvents

N,N-dimethylformamide

tetrahydrofuran

Conditions

Workup

1. 1
   FiltrationThe reaction was worked up by filtration through a syringe
2. 2
   Filtrationfilter
3. 3
   Concentrationconcentrated
4. 4
   Otherthe crude product was purified by preparative HPLC
5. 5
   OtherThis resulted in the product with the molecular weight of 471.6 (C29H33N3O3)

Procedure

5-Bromofuran-2-carboxylic acid [4-(3-dimethylaminopyrrolidin-1-yl)phenyl]amide (75 mg) was dissolved together with 1-butoxy-4-ethynylbenzene (35 mg) in N,N-dimethylformamide (1 ml) and, under argon, added dropwise to a suspension of Pd(tBu3P)2Cl2 (4 mg), copper (I) iodide (75 mg) and N,N-diisopropylamine (20 mg) in anhydrous tetrahydrofuran (3 ml). The mixture was stirred at room temperature for 8 hours. The reaction was worked up by filtration through a syringe filter and concentrated, and the crude product was purified by preparative HPLC. This resulted in the product with the molecular weight of 471.6 (C29H33N3O3); MS (ESI): 472 (M+H+) as hydrotrifluoroacetate.

Source