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

HRID 384415

반응식

HRID 384415 반응식
[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]

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

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.

후처리

  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

출처 및 근거

ORD 기록
ord-cada8371c8d248ec8708bec18c1100ae
출처 데이터셋
uspto-grants-2013_02
특허 번호
US08367710B2

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