p-Toluenesulfonic acid → 3-[1-(1-Methyl-piperidin-4-yl)-indol-3-yl]-4-(1-methyl-indol-3-yl)-1H-pyrrole-2,5-dione

HRID 1378532ノート

反応式

HRID 1378532 の反応式
[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[CH:10]=[CH:9]2)[CH2:4][CH2:3]1.[C:17](Cl)(=[O:21])[C:18](Cl)=O.Cl.[C:24](=[NH:27])([OH:26])[CH3:25].[CH2:28]([N:30]([CH2:33][CH3:34])[CH2:31][CH3:32])C.[C:35]1(C)[CH:40]=CC(S(O)(=O)=O)=[CH:37][CH:36]=1.C(=O)([O-])O.[Na+]>CCOCC>[CH3:1][N:2]1[CH2:7][CH2:6][CH:5]([N:8]2[C:16]3[C:11](=[CH:12][CH:13]=[CH:14][CH:15]=3)[C:10]([C:25]3[C:24](=[O:26])[NH:27][C:17](=[O:21])[C:18]=3[C:32]3[C:34]4[C:33](=[CH:40][CH:35]=[CH:36][CH:37]=4)[N:30]([CH3:28])[CH:31]=3)=[CH:9]2)[CH2:4][CH2:3]1

参加物

8

反応物 6

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 65578Oxalyl chlorideHCID 516892Sodium BicarbonateHCID 140907431-(1-methyl-piperidin-4-yl)-1H-indoleHCID 178465697HCID 178465697、化合物

生成物 1

HCID 98893513-[1-(1-Methyl-piperidin-4-yl)-indol-3-yl]-4-(1-methyl-indol-3-yl)-1H-pyrrole-2,5-dione収率 41.5%

試薬・触媒・溶媒 1

HCID 3283Diethyl Ether溶媒

実験手順

To an ice cooled solution of 1-(1-methyl-piperidin-4-yl)-1H-indole (38 g, 0.177 mol) in dry ether (1.2 L) was added oxalyl chloride (16.7 mL, 0.195 mol) dropwise at a rate such that the internal temperature does not exceed 5° C. Stirring at 0° to 5° C. is continued for 30 minutes. A yellow precipitate was isolated by suction filtration, washed with ether (800 mL) and suspended in methylene chloride (1.5 L). The solution was recooled to 0° to 5° C. and treated with isopropyl(1-methyl)indol-3-yl)acetimidate hydrochloride (49.6 g, 0.186 mol) in one portion followed by dropwise addition of triethylamine (123 mL, 0.885 mol). The reaction was brought to ambient temperature and stirred for 3 hours. Anhydrous p-toluene sulfonic acid (152.4 g) was added in several portions with external cooling and stirring was continued for 30 minutes. The mixture was poured into saturated aqueous sodium hydrogen carbonate (2 L) and shaken. A bright orange precipitate (32.2 g) formed which was isolated by suction filtration and washed successively with water, dioxane, and ether. A second crop was isolated by evaporation of the mother liquor and trituration with dioxane (9.4 g). Total yield: 41.6 g (54% of theory). M.Pt.: 316°-318° C.

後処理

  1. customdoes not exceed 5° C
  2. customA yellow precipitate was isolated by suction filtration
  3. washwashed with ether (800 mL)
  4. customwas recooled to 0° to 5° C.
  5. customwas brought to ambient temperature
  6. stirringstirred for 3 hours
  7. temperaturewith external cooling
  8. stirringstirring
  9. waitwas continued for 30 minutes
  10. stirringshaken

出典と根拠

ORDレコード
ord-f5977992a7584d3ea5a5049cb0d9b7c2
出典データセット
uspto-grants-1997_09
特許番号
US05668152

反応ノート

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