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

HRID 79482ノート

反応式

HRID 79482 の反応式
[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

参加物

7

反応物 4

HCID 11430Potassium CarbonateHCID 24386Thionyl ChlorideHCID 123972613-Benzyloxy-6-hydroxymethyl-2-methylpyridineHCID 178526560HCID 178526560、化合物

生成物 1

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

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 6344Dichloromethane溶媒

実験手順

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%).

後処理

  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)

出典と根拠

ORDレコード
ord-5ca63e5a6a2a410ba292af5813414422
出典データセット
uspto-grants-2014_09
特許番号
US08841455B2

反応ノート

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