p-Toluenesulfonic acid → Methyl 4-iodo-1-tosyl-1H-pyrrole-2-carboxylate

HRID 384415

反応式

HRID 384415 の反応式
[CH3:1][O:2][C:3]([C:5]1[NH:6][CH:7]=[C:8]([I:10])[CH:9]=1)=[O:4].C(N(CC)CC)C.[C:18]1([CH3:28])[CH:23]=[CH:22][C:21]([S:24](O)(=[O:26])=[O:25])=[CH:20][CH:19]=1>ClCCl.CN(C)C1C=CN=CC=1>[CH3:1][O:2][C:3]([C:5]1[N:6]([S:24]([C:21]2[CH:22]=[CH:23][C:18]([CH3:28])=[CH:19][CH:20]=2)(=[O:26])=[O:25])[CH:7]=[C:8]([I:10])[CH:9]=1)=[O:4]

参加物

6

反応物 3

HCID 6101p-Toluenesulfonic acidHCID 8471TriethylamineHCID 11673249methyl 4-iodo-1H-pyrrole-2-carboxylate

生成物 1

HCID 59694429Methyl 4-iodo-1-tosyl-1H-pyrrole-2-carboxylate収率 80.2%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

4-Iodo-1H-pyrrole-2-carboxylic acid methyl ester 57d (25.1 g, 100 mmol) was dissolved in 150 mL of dichloromethane followed by addition of triethylamine (30.6 mL, 220 mmol), 4-dimethylaminopyridine (1.22 g, 10 mmol) and p-toluenesulfonic acid (21 g, 110 mmol). The reaction mixture was reacted at 20° C. overnight. The reaction was monitored by TLC until the disappearance of the starting materials and quenched by addition of 30 mL of hydrochloric acid (1 N). The mixture was extracted with dichloromethane (50 mL×3). The combined organic extracts were washed with saturated aqueous sodium carbonate and saturated brine successively, dried over anhydrous sodium sulfate, filtered to remove the drying agent and concentrated under reduced pressure. The residue was purified by silica gel column chromatography to obtain the title compound 4-iodo-1-(toluene-4-sulfonyl)-1H-pyrrole-2-carboxylic acid methyl ester 57e (32.5 g, yield 80.2%) as a white solid.

後処理

  1. customThe reaction mixture was reacted at 20° C. overnight
  2. customquenched by addition of 30 mL of hydrochloric acid (1 N)
  3. extractionThe mixture was extracted with dichloromethane (50 mL×3)
  4. washThe combined organic extracts were washed with saturated aqueous sodium carbonate and saturated brine successively
  5. dry with materialdried over anhydrous sodium sulfate
  6. filtrationfiltered
  7. customto remove the drying agent
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel column chromatography

出典と根拠

ORDレコード
ord-cada8371c8d248ec8708bec18c1100ae
出典データセット
uspto-grants-2013_02
特許番号
US08367710B2

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