反応 #42449

反応方程式

methyl 4-[methyl(methylsulfonyl)amino]-1H-indole-6-carboxylate

potassium hydroxide

iodobutane

→

title compound

1-Butyl-4-[methyl(methylsulfonyl)amino]-1H-indole-6-carboxylic acid

溶媒

DMF

反応条件

後処理

1. 1
   その他The mixture was partitioned between water and ethyl acetate
2. 2
   その他the layers were separated
3. 3
   洗浄the organic layer washed three times with water
4. 4
   乾燥The organic layer was dried over anhydrous sodium sulfate
5. 5
   ろ過filtered
6. 6
   濃縮concentrated
7. 7
   workup.DISSOLUTIONThe residue was dissolved in methanol (5 mL) to which
8. 8
   workup.ADDITIONwas added 1N NaOH (2 mL)
9. 9
   温度the mixture heated to 50° C. for 1 h
10. 10
    温度The mixture was cooled to room temperature
11. 11
    workup.ADDITIONpoured into water
12. 12
    洗浄washed with ether
13. 13
    抽出the product extracted into ethyl acetate which
14. 14
    乾燥was dried over anhydrous sodium sulfate
15. 15
    ろ過filtered
16. 16
    濃縮concentrated to dryness

実験手順

To a mixture of methyl 4-[methyl(methylsulfonyl)amino]-1H-indole-6-carboxylate (0.437 g) in DMF (15 mL) was added potassium hydroxide (0.087 g) and iodobutane (0.34 mL). The mixture was heated to 70° C. for 6 h. then stirred at room temperature for 72 h. The mixture was partitioned between water and ethyl acetate, the layers were separated and the organic layer washed three times with water. The organic layer was dried over anhydrous sodium sulfate, filtered and concentrated. The residue was dissolved in methanol (5 mL) to which was added 1N NaOH (2 mL) and the mixture heated to 50° C. for 1 h. The mixture was cooled to room temperature and poured into water and washed with ether. The aqueous layer was acidified to pH 4 with 1N HCl and the product extracted into ethyl acetate which was dried over anhydrous sodium sulfate, filtered and concentrated to dryness to give 0.377 g of the title compound: 1H NMR (CDCl3) δ 0.973, 1.38, 1.87, 3.01, 3.45, 4.21, 6.71, 7.36, 7.82, 8.18.

出典