Reaktion #67189

ord-109563af41044050b46ecc30841e6c23

Reaktionsgleichung

Cc1ccc(S(=O)(=O)OCC2COc3c(F)cc(S(C)(=O)=O)cc3O2)cc1
[5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate
CN
methanamine
→
CNCC1COc2c(F)cc(S(C)(=O)=O)cc2O1
title compound
CNCC1COc2c(F)cc(S(C)(=O)=O)cc2O1
1-[5-FLUORO-7-(METHYLSULFONYL)-2,3-DIHYDRO-1,4-BENZODIOXIN-2-YL]-N-METHYLMETHANAMINE

Edukte

Cc1ccc(S(=O)(=O)OCC2COc3c(F)cc(S(C)(=O)=O)cc3O2)cc1
[5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate
CN
methanamine

Reagenzien

Keine

Lösungsmittel

CC#N
ACN

Reaktionsbedingungen

Temperatur
120°CELSIUS
Detaillierte Bedingungen
See reaction.notes.procedure_details.

Aufarbeitung

  1. 1
    SonstigePurification on flash column chromatography (EtOAc/MeOH)

Vorschrift

A mixture of [5-fluoro-7-(methylsulfonyl)-2,3-dihydro-1,4-benzodioxin-2-yl]methyl 4-methylbenzenesulfonate (0.4 g, 1 mmol), methanamine (1 ml, 40% in water) and ACN (3 ml) was heated under microwave radiation at 120° C. for 20 min. Purification on flash column chromatography (EtOAc/MeOH) gave the title compound. Yield: 0.2 g, 69%. The amine was converted to the hydrochloric acid salt and crystallized from EtOH/Et2O. M.p. 243° C. MS m/z (rel. intensity, 70 eV) 275 (M+, 81), 97 (48), 70 (bp), 69 (73), 63 (58).

Quelle

DOI: 10.6084/m9.figshare.5104873.v1Patent: US08524766B2uspto-grants-2013_09