Water → 1-(Methoxymethyl)-7-nitro-2-(1,3-thiazol-2-yl)-1H-indole

HRID 1851369ノート

反応式

HRID 1851369 の反応式
[H-].[Na+].[N+:3]([C:6]1[CH:7]=[CH:8][CH:9]=[C:10]2[C:14]=1[NH:13][C:12]([C:15]1[S:16][CH:17]=[CH:18][N:19]=1)=[CH:11]2)([O-:5])=[O:4].[CH3:20][O:21][CH2:22]Cl.O>CN(C)C=O.O1CCCC1>[CH3:20][O:21][CH2:22][N:13]1[C:14]2[C:10](=[CH:9][CH:8]=[CH:7][C:6]=2[N+:3]([O-:5])=[O:4])[CH:11]=[C:12]1[C:15]1[S:16][CH:17]=[CH:18][N:19]=1

参加物

7

反応物 4

HCID 962WaterHCID 7864Chloromethyl Methyl EtherHCID 24758Sodium hydrideHCID 579018457-Nitro-2-(1,3-thiazol-2-yl)-1H-indole

生成物 1

HCID 579018301-(Methoxymethyl)-7-nitro-2-(1,3-thiazol-2-yl)-1H-indole収率 82%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a suspension of sodium hydride (60% in oil, 0.47 g) in N,N-dimethylformamide (15 mL) was slowly added 7-nitro-2-(1,3-thiazol-2-yl)-1H-indole (2.21 g) at 0° C., and the mixture was stirred for 20 min. To the reaction mixture was added a solution of chloromethyl methyl ether (0.81 mL) in tetrahydrofuran (2 mL) at 0° C. over 20 min, and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The ethyl acetate layer was washed with saturated brine, dried (MgSO4) and concentrated. The obtained residue was subjected to silica gel column chromatography and the title compound (2.14 g, yield 82%) was obtained as a yellow oil from a fraction eluted with ethyl acetate-hexane (1:2, volume ratio).

後処理

  1. customat 0° C.
  2. stirringthe mixture was stirred at room temperature overnight
  3. extractionthe mixture was extracted with ethyl acetate
  4. washThe ethyl acetate layer was washed with saturated brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated

出典と根拠

ORDレコード
ord-1c150a54064a44c09bc5c61afcc039c8
出典データセット
uspto-grants-2015_02
特許番号
US08957070B2

反応ノート

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