Réaction #88086

Équation de réaction

4-iodo-1-isopropyl-1H-indazole-6-carboxylic acid methyl ester

5-methyl-pyridinyl zinc bromide

→

1-isopropyl-4-(5-methyl-pyridin-2-yl)-1H-indazole-6-carboxylic acid methyl ester

Rendement 50.0%

Solvants

THF

THF

Conditions de réaction

Traitement

1. 1
   Autrequenched by addition of saturated aqueous NH4Cl solution
2. 2
   AutreThe mixture was partitioned between water and ethyl acetate
3. 3
   Autrethe organic layer was separated
4. 4
   Séchagedried over MgSO4
5. 5
   Filtrationfiltered
6. 6
   Concentrationconcentrated under reduced pressure
7. 7
   AutrePurification by column chromatography

Mode opératoire

To a solution of 4-iodo-1-isopropyl-1H-indazole-6-carboxylic acid methyl ester (1.13 g, 3.28 mmol) in THF (30 mL) was added Pd(PPh3)4 (0.2 g, 0.164 mmol), followed by 5-methyl-pyridinyl zinc bromide ((19.7 mL of 0.5M solution in THF, 9.86 mmol). The reaction mixture was stirred overnight at room temperature, then quenched by addition of saturated aqueous NH4Cl solution. The mixture was partitioned between water and ethyl acetate, and the organic layer was separated, dried over MgSO4, filtered and concentrated under reduced pressure. Purification by column chromatography gave 0.5 g (50%) of 1-isopropyl-4-(5-methyl-pyridin-2-yl)-1H-indazole-6-carboxylic acid methyl ester.

Source