Potassium Carbonate → 3-iodo-1-((2-methoxy-6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole

HRID 79275노트

반응식

HRID 79275 반응식
Br[CH2:2][C:3]1[C:4]([O:10][CH3:11])=[N:5][C:6]([CH3:9])=[CH:7][CH:8]=1.[I:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[N+:22]([O-:24])=[O:23])[NH:15][N:14]=1.C(=O)([O-])[O-].[K+].[K+]>CN(C)C=O.O>[I:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[N+:22]([O-:24])=[O:23])[N:15]([CH2:2][C:3]2[C:4]([O:10][CH3:11])=[N:5][C:6]([CH3:9])=[CH:7][CH:8]=2)[N:14]=1

참가 물질

6

반응물 3

HCID 11430Potassium CarbonateHCID 672536903-(Bromomethyl)-2-methoxy-6-methylpyridineHCID 178526562HCID 178526562, 화합물

생성물 1

HCID 672596093-iodo-1-((2-methoxy-6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole수율 101.9%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매

실험 절차

A mixture of 3-(bromomethyl)-2-methoxy-6-methylpyridine (500 mg, 2.314 mmol) and 3-iodo-4-nitro-1H-indazole (668.8 mg, 2.314 mmol) (prepared as in Example 1, step E) was dissolved in dry N,N-dimethylformamide (11.6 mL) with stirring under an atmosphere of nitrogen. Potassium carbonate (479.7 mg, 3.471 mmol) was added and the mixture was stirred at ambient temperature for 16 hours. The mixture was diluted with water (50 mL) and extracted into ethyl acetate. The combined organic extracts were washed with brine and dried over sodium sulfate. The solution was filtered and concentrated under reduced pressure to give 3-iodo-1-((2-methoxy-6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole (1.0 g) which was used without purification.

후처리

  1. stirringthe mixture was stirred at ambient temperature for 16 hours
  2. extractionextracted into ethyl acetate
  3. washThe combined organic extracts were washed with brine
  4. dry with materialdried over sodium sulfate
  5. filtrationThe solution was filtered
  6. concentrationconcentrated under reduced pressure

출처 및 근거

ORD 기록
ord-c33da889509744e6a56cbac7b0370f41
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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