Reaktion #649255

ord-8b498e08f4854a79bef8f180e146f092

Reaktionsgleichung

CC(=O)O[BH-](OC(C)=O)OC(C)=O.[Na+]
Sodium triacetoxyborohydride
CCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(-c4csc(C=O)c4)cc23)CC1
3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide
c1ccc(C2CCCN2)cc1
2-phenylpyrrolidine
CCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(-c4csc(CN5CCCC5c5ccccc5)c4)cc23)CC1
title compound
Ausbeute 22.1%
CCS(=O)(=O)N1CCC(c2c[nH]c3c(C(N)=O)cc(-c4csc(CN5CCCC5c5ccccc5)c4)cc23)CC1
3-[1-(ethylsulfonyl)-4-piperidinyl]-5-{5-[(2-phenyl-1-pyrrolidinyl)methyl]-3-thienyl}-1H-indole-7-carboxamide
Ausbeute 22.1%

Lösungsmittel

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigeThe reaction mixture was then reacted in a microwave at 120° C. for 10 min
  2. 2
    Sonstigethe reaction was reacted at room temperature overnight
  3. 3
    SonstigeIt was then purified by Gilson Preparatory HPLC

Vorschrift

To a solution of 3-[1-(ethylsulfonyl)-4-piperidinyl]-5-(5-formyl-3-thienyl)-1H-indole-7-carboxamide (50 mg, 0.11 mmol) in DMSO (2.0 mL) was added 2-phenylpyrrolidine (147 mg, 1.0 mmol). The reaction mixture was then reacted in a microwave at 120° C. for 10 min. Sodium triacetoxyborohydride (220 mg, 1.0 mmol) was then added and the reaction was reacted at room temperature overnight. It was then purified by Gilson Preparatory HPLC to give 14.0 mg of the title compound (22%).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08063071B2uspto-grants-2011_11