Reaktion #961855

Reaktionsgleichung

NaHCO3 DCM

DIEA

5-(2-fluoro-6-methylbenzo[b]furan-5-yl)-2-pyridylamine

2,6-difluorobenzoyl chloride

→

(2,6-difluorophenyl)-N-[5-(2-fluoro-6-methylbenzo[b]furan-5-yl)(2-pyridyl)]carboxamide

Ausbeute 68.6%

Lösungsmittel

DCM

Reaktionsbedingungen

Aufarbeitung

1. 1
   WaschenDCM phase was washed with brine
2. 2
   Einengenconcentrated to dryness
3. 3
   workup.DISSOLUTIONThe residue was dissolved in 3 ml THF/MeOH/H2O (5:4:1)
4. 4
   workup.STIRRINGstirred with 1N NaOH (200 μl) at r.t. for 2 h

Vorschrift

To a solution of 5-(2-fluoro-6-methylbenzo[b]furan-5-yl)-2-pyridylamine (231) (23 mg, 0.095 mmol) in 3 ml DCM was added 2,6-difluorobenzoyl chloride (36 μl, 3 eq) followed by addition of DIEA (149 μl). The resulting solution was stirred overnight at r.t. The reaction mixture was worked up with aq. NaHCO3/DCM. DCM phase was washed with brine, concentrated to dryness. The residue was dissolved in 3 ml THF/MeOH/H2O (5:4:1) and stirred with 1N NaOH (200 μl) at r.t. for 2 h before worked up with EA/aq. NaHCO3. Silica gel flash chromatography furnished (2,6-difluorophenyl)-N-[5-(2-fluoro-6-methylbenzo[b]furan-5-yl)(2-pyridyl)]carboxamide (223) (24.9 mg, yield: 68.6%, purity>95%) as white solid.

Quelle