Reaktion #680803

ord-9bfe6d88a8604e719d6437e919a16ff1

Reaktionsgleichung

CN(C)C=O
DMF
Cn1c(-c2cncc(C(N)(C(=O)OC(C)(C)C)S(C)(=O)=O)c2)cc2ccccc21
2-[5-(methanesulfonyl-(tert-butoxycarbonyl)-amino-methyl)-pyridin-3-yl]-1-methyl-indole
O=C=NS(=O)(=O)Cl
chlorosulfonyl isocyanate
→
Cn1c(-c2cncc(C(N)(C(=O)OC(C)(C)C)S(C)(=O)=O)c2)c(C#N)c2ccccc21
2-[5-(methanesulfonyl-(tert-butoxycarbonyl)-amino-methyl)-pyridin-3-yl]-1-methyl-3-cyano-indole

Edukte

CN(C)C=O
DMF
Cn1c(-c2cncc(C(N)(C(=O)OC(C)(C)C)S(C)(=O)=O)c2)cc2ccccc21
2-[5-(methanesulfonyl-(tert-butoxycarbonyl)-amino-methyl)-pyridin-3-yl]-1-methyl-indole
O=C=NS(=O)(=O)Cl
chlorosulfonyl isocyanate

Reagenzien

Keine

Lösungsmittel

ClCCl
dichloromethane

Reaktionsbedingungen

Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    workup.ADDITIONis added
  2. 2
    Einengenthe mixture is concentrated to a volume of 3 mL
  3. 3
    Filtrationfiltered
  4. 4
    SonstigePurification by RP HPLC

Vorschrift

To a solution of 2-[5-(methanesulfonyl-(tert-butoxycarbonyl)-amino-methyl)-pyridin-3-yl]-1-methyl-indole (350 mg, 0.842 mmol) in dichloromethane (10 mL) is added chlorosulfonyl isocyanate (0.358 g, 2.53 mmol). The mixture is stirred at ambient temperature for 20 min, whereupon anhydrous DMF (2 mL) is added. After 1 h, the mixture is concentrated to a volume of 3 mL, and filtered. Purification by RP HPLC affords 2-[5-(methanesulfonyl-(tert-butoxycarbonyl)-amino-methyl)-pyridin-3-yl]-1-methyl-3-cyano-indole. MS (ESI) m/z 441.1 (M+H)+.

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US09242963B2uspto-grants-2016_01