反応 #88086

反応方程式

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

収率 50.0%

溶媒

THF

THF

反応条件

後処理

1. 1
   その他quenched by addition of saturated aqueous NH4Cl solution
2. 2
   その他The mixture was partitioned between water and ethyl acetate
3. 3
   その他the organic layer was separated
4. 4
   乾燥dried over MgSO4
5. 5
   ろ過filtered
6. 6
   濃縮concentrated under reduced pressure
7. 7
   その他Purification by column chromatography

実験手順

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.

出典