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

HRID 348960

反応式

HRID 348960 の反応式
[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]

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

反応条件

温度
60 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-bbf755d5c106475a89061efcce26d471
出典データセット
uspto-grants-2007_02
特許番号
US07176242B2

関連ノート

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