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

HRID 79482Notes

Reaction equation

HRID 79482 reaction equation
[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

Participants

7

Reactant 4

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

Product 1

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

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 6344DichloromethaneSolvent

Procedure

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%).

Workup

  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)

Sources & evidence

ORD record
ord-5ca63e5a6a2a410ba292af5813414422
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

Loading…