Hydrochloric Acid → N-(1-benzyl-1H-indole-5-yl)-methanesulfonamide

HRID 1359138ノート

反応式

HRID 1359138 の反応式
[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([N+:17]([O-])=O)=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C([O-])=O.[NH4+].[S:24](Cl)([CH3:27])(=[O:26])=[O:25].C(N(CC)CC)C.Cl>O1CCCC1.CO.[Pd]>[CH2:1]([N:8]1[C:16]2[C:11](=[CH:12][C:13]([NH:17][S:24]([CH3:27])(=[O:26])=[O:25])=[CH:14][CH:15]=2)[CH:10]=[CH:9]1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

参加物

9

反応物 5

HCID 313Hydrochloric AcidHCID 8471TriethylamineHCID 31297Methanesulfonyl chlorideHCID 2723923Ammonium formateHCID 98563511-Benzyl-5-nitro-1H-indole

生成物 1

HCID 9944156N-(1-benzyl-1H-indole-5-yl)-methanesulfonamide収率 34%

試薬・触媒・溶媒 3

HCID 23938Palladium触媒HCID 887Methanol溶媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
30 °C

実験手順

1-benzyl-5-nitro-1H-indole (50 mg, 0.19 mmol) was dissolved in tetrahydrofuran (1 ml) and methanol (1 ml), and ammonium formate of an excess amount and palladium/carbon (10%) of a catalytic amount were added. The solution was stirred at around 30° C. for 30 minutes to complete the reduction, filtrated through celite, concentrated under reduced pressure, dissolved again in dichloromethane (10 ml), and then washed with water and brine. After drying the resulting solution over anhydrous magnesium sulfate, dichloromethane solution containing amine compound (1-benzyl-5-amino-1H-indole) was obtained. Mesyl chloride (0.015 ml, 0.19 mmol) and triethylamine (0.028 ml, 0.20 mmol) were added to the above obtained solution and stirred at room temperature for 2 hours to complete the reaction. After adding 2N-hydrochloric acid solution (10 ml) to separate layers, dichloromethane solution was induced, washed by using water and brine, dried over anhydrous magnesium sulfate, concentrated under reduced pressure, and then triturated with isooctane and isopropyleter. As a result, the present compound (34mg, productive yield 34%) was obtained as a solid.

後処理

  1. filtrationfiltrated through celite
  2. concentrationconcentrated under reduced pressure
  3. dissolutiondissolved again in dichloromethane (10 ml)
  4. washwashed with water and brine
  5. dry with materialAfter drying the resulting solution over anhydrous magnesium sulfate, dichloromethane solution
  6. additioncontaining amine compound (1-benzyl-5-amino-1H-indole)
  7. customwas obtained
  8. stirringstirred at room temperature for 2 hours
  9. customthe reaction
  10. customto separate layers, dichloromethane solution
  11. washwashed
  12. dry with materialdried over anhydrous magnesium sulfate
  13. concentrationconcentrated under reduced pressure
  14. customtriturated with isooctane and isopropyleter
  15. customAs a result, the present compound (34mg, productive yield 34%) was obtained as a solid

出典と根拠

ORDレコード
ord-5d66e3a4745b49dc9d554538dcbcda0d
出典データセット
uspto-grants-2003_07
特許番号
US06599929B2

反応ノート

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