Potassium Carbonate → 1-((5-(benzyloxy)-6-methylpyridin-2-yl)methyl)-3-bromo-4-nitro-1H-indazole

HRID 79482노트

반응식

HRID 79482 반응식
[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:16]O)=[N:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.S(Cl)(Cl)=O.[Br:22][C:23]1[C:31]2[C:26](=[CH:27][CH:28]=[CH:29][C:30]=2[N+:32]([O-:34])=[O:33])[NH:25][N:24]=1.C([O-])([O-])=O.[K+].[K+]>C(Cl)Cl.CN(C=O)C>[CH2:1]([O:8][C:9]1[CH:10]=[CH:11][C:12]([CH2:16][N:25]2[C:26]3[C:31](=[C:30]([N+:32]([O-:34])=[O:33])[CH:29]=[CH:28][CH:27]=3)[C:23]([Br:22])=[N:24]2)=[N:13][C:14]=1[CH3:15])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

7

반응물 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 123972613-Benzyloxy-6-hydroxymethyl-2-methylpyridineHCID 178526560HCID 178526560, 화합물

생성물 1

HCID 672601791-((5-(benzyloxy)-6-methylpyridin-2-yl)methyl)-3-bromo-4-nitro-1H-indazole수율 87%

시약·촉매·용매 2

HCID 6228Dimethylformamide용매HCID 6344Dichloromethane용매

실험 절차

To (5-(benzyloxy)-6-methylpyridin-2-yl)methanol (3.51 g, 15.3 mmol, Prepared as described in U.S. Pat. No. 3,952,101) in DCM (10 mL) was added sulfurous dichloride (10.9 g, 91.9 mmol). The reaction mixture was stirred for 3 hours, and then solvent was removed under reduced pressure. To the resulting solid was added 3-bromo-4-nitro-1H-indazole (3.71 g, 15.3 mmol), K2CO3 (6.35 g, 45.9 mmol) and anhydrous DMF (20 mL). The reaction mixture was stirred for 18 hours. The solvent was removed under reduced pressure. The residue was diluted with water (50 mL) and extracted with EtOAc. The combined organic extracts were dried (Na2SO4), and concentrated, and the residue was purified by silica gel flash chromatography (1:3 EtOAc/hexanes) to give desired product (87%).

후처리

  1. customsolvent was removed under reduced pressure
  2. stirringThe reaction mixture was stirred for 18 hours
  3. customThe solvent was removed under reduced pressure
  4. additionThe residue was diluted with water (50 mL)
  5. extractionextracted with EtOAc
  6. dry with materialThe combined organic extracts were dried (Na2SO4)
  7. concentrationconcentrated
  8. customthe residue was purified by silica gel flash chromatography (1:3 EtOAc/hexanes)

출처 및 근거

ORD 기록
ord-5ca63e5a6a2a410ba292af5813414422
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841455B2

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