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

HRID 16628

반응식

HRID 16628 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 8857Ethyl Acetate용매

실험 절차

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%).

후처리

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

출처 및 근거

ORD 기록
ord-02e4b9ab0bf74da998fa4be994fe94f7
출처 데이터셋
uspto-grants-2010_06
특허 번호
US07737173B2

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