Methanesulfonyl chloride → Methyl 4-[(methylsulfonyl)amino]-1H-indole-6-carboxylate

HRID 14169

반응식

HRID 14169 반응식
[NH2:1][C:2]1[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[CH3:15][S:16](Cl)(=[O:18])=[O:17]>CN(C=O)C.CN(C)C1C=CN=CC=1>[CH3:15][S:16]([NH:1][C:2]1[CH:10]=[C:9]([C:11]([O:13][CH3:14])=[O:12])[CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2)(=[O:18])=[O:17]

참가 물질

5

반응물 2

HCID 31297Methanesulfonyl chlorideHCID 14243967Methyl 4-amino-1H-indole-6-carboxylate

생성물 1

HCID 21086208Methyl 4-[(methylsulfonyl)amino]-1H-indole-6-carboxylate수율 50.5%

시약·촉매·용매 2

HCID 142844-(Dimethylamino)pyridine촉매HCID 6228Dimethylformamide용매

반응 조건

온도
60 °C

실험 절차

To a mixture of methyl 4-amino-1H-indole-6-carboxylate (1.0 g) in DMF (10 mL) was added 4-dimethylaminopyridine (1.46 g) and methanesulfonyl chloride (0.6 g). The mixture was heated to 60° C. for 3 h, cooled to room temperature, and partitioned between water and ethyl acetate. The layers were separated and the organic layer washed three times with brine, dried over anhydrous sodium sulfate and concentrated to give 0.71 g of the title compound: 1H NMR (CDCl3) δ 3.02, 3.94, 6.69, 7.42, 7.81, 8.04.

후처리

  1. temperaturecooled to room temperature
  2. custompartitioned between water and ethyl acetate
  3. customThe layers were separated
  4. washthe organic layer washed three times with brine
  5. dry with materialdried over anhydrous sodium sulfate
  6. concentrationconcentrated

출처 및 근거

ORD 기록
ord-af7cd9f759014a5f8832d2a50b3f6f11
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07727997B2

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