Reacción #2358512

ord-431ad34447f24423912fab3da84bc922

Ecuación de reacción

CS(=O)(=O)c1cc(F)cc(OCCBr)c1
1-(2-bromoethoxy)-3-fluoro-5-methylsulfonyl-benzene
CCC(C)(C)N
tert-amylamine
CCC(C)(C)NCCOc1cc(F)cc(S(C)(=O)=O)c1
title compound
Rendimiento 76.3%
CCC(C)(C)NCCOc1cc(F)cc(S(C)(=O)=O)c1
N-[2-(3-fluoro-5-methylsulfonyl-phenoxy)ethyl]-2-methyl-butan-2-amine
Rendimiento 76.3%

Disolventes

Condiciones de reacción

Condiciones detalladas
See reaction.notes.procedure_details.

Tratamiento posterior

  1. 1
    OtroPreparation
  2. 2
    OtroPurification by flash column chromatography (ethyl acetate/methanol, 100:0 to 85:15)

Procedimiento

Preparation according to Example 1 but performed in one portion: 1-(2-bromoethoxy)-3-fluoro-5-methylsulfonyl-benzene (0.5 g, 1.68 mmol) and tert-amylamine (1.61 ml, 13.46 mmol) in ethanol (5 ml). Purification by flash column chromatography (ethyl acetate/methanol, 100:0 to 85:15) gave the title compound (389 mg, 76.2%). The amine was converted to the hydrochloric acid salt and re-crystallized from methanol/diethyl ether: M.p. 190.2° C. MS m/z (relative intensity, 70 eV) 303 (M+, 0), 288 (21), 276 (10), 275 (41), 274 (bp), 84 (10).

Fuente

DOI: 10.6084/m9.figshare.5104873.v1Patente: US09120728B2uspto-grants-2015_09