Benzyl Bromide → 1-benzyl-2-methyl-5-nitro-1H-indole-3-carboxaldehyde

HRID 16628

反応式

HRID 16628 の反応式
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([C:10]=1[CH:11]=[O:12])=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6][CH:5]=2.C(=O)([O-])[O-].[K+].[K+].[CH2:22](Br)[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1>CN(C=O)C.CCOC(C)=O>[CH2:22]([N:3]1[C:4]2[C:9](=[CH:8][C:7]([N+:13]([O-:15])=[O:14])=[CH:6][CH:5]=2)[C:10]([CH:11]=[O:12])=[C:2]1[CH3:1])[C:23]1[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=1

参加物

6

反応物 3

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 6093592-methyl-5-nitro-1H-indole-3-carbaldehyde

生成物 1

HCID 28382531-benzyl-2-methyl-5-nitro-1H-indole-3-carboxaldehyde収率 83.2%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of 2-methyl-5-nitro-1H-indole-3-carboxaldehyde (500 mg, 2.45 mmol) in DMF (5 ml) was added potassium carbonate (1.0 g, 7.35 mmol) and benzyl bromide (0.44 ml, 3.68 mmol). The mixture was stirred at room temperature for 4 h, diluted with EtOAc, washed with H2O, brine, dried over Na2SO4, and concentrated under reduced pressure. The residue was triturated with Et2O-hexane to yield 1-benzyl-2-methyl-5-nitro-1H-indole-3-carboxaldehyde (Compound 50) as a yellow solid (600 mg, 83%).

後処理

  1. washwashed with H2O, brine
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. customThe residue was triturated with Et2O-hexane

出典と根拠

ORDレコード
ord-02e4b9ab0bf74da998fa4be994fe94f7
出典データセット
uspto-grants-2010_06
特許番号
US07737173B2

関連ノート

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