Réaction #540244

Équation de réaction

2-Bromo-pyridin-4-ylamine

NaH

4-Fluoro-3-nitro-benzoic acid methyl ester

→

3

Rendement 85.2%

4-(2-bromo-pyridin-4-ylamino)-3-nitro-benzoic Acid Methyl Ester

Rendement 85.2%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   Autrewas at 0° C.
2. 2
   Autreto reach RT
3. 3
   Autrethe reaction was quenched by addition of iPrOH and H2O
4. 4
   AutreA precipitate was formed
5. 5
   Filtrationthis was filtered off
6. 6
   Autredried

Mode opératoire

2-Bromo-pyridin-4-ylamine 2 (4.3 g; 25 mmol) and NaH 60% (1.5 g; 37 mmol) was at 0° C. stirred for 1 h in dry THF (50 ml) and then a solution of 4-Fluoro-3-nitro-benzoic acid methyl ester 1 (5 g; 25 mmol) in dry THF (50 ml) was addeddrop. The resulting cold solution was allowed to reach RT and stirred overnight for completion of the reaction. LCMS showed complete conversion to product and the reaction was quenched by addition of iPrOH and H2O. A precipitate was formed and this was filtered off, dried under educed pressure to obtain 3 as a yellow solid (7.5 g). Yield 85%. The product identity was confirmed by NMR and LCMS and taken for the next step.

Source