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

HRID 706726Notes

Reaction equation

HRID 706726 reaction equation
[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[NH:4][N:3]=1.Cl.Cl[CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]([CH3:25])[CH3:24])[N:18]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[Br:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][C:9]=2[N+:11]([O-:13])=[O:12])[N:4]([CH2:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([CH:23]([CH3:25])[CH3:24])[N:18]=2)[N:3]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 679741532-(Chloromethyl)-6-isopropylpyridine hydrochlorideHCID 178526560HCID 178526560, compound

Product 1

HCID 679758823-bromo-1-((6-isopropylpyridin-2-yl)methyl)-4-nitro-1H-indazoleYield 67%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To 3-bromo-4-nitro-1H-indazole (4.91 g, 20.3 mmol) in DMF (50 mL) was added 2-(chloromethyl)-6-isopropylpyridine hydrochloride (4.18 g, 20.3 mmol) and K2CO3 (8.41 g, 60.8 mmol). The reaction mixture was stirred for 18 hours. Solvent was removed under reduced pressure. The residue was diluted with EtOAc (100 mL). The resulting suspension was washed with water and brine. The combined organic extracts were dried (Na2SO4), filtered and purified by silica gel flash chromatography (1:2 EtOAc/hexanes) to give the desired product (67%).

Workup

  1. customSolvent was removed under reduced pressure
  2. additionThe residue was diluted with EtOAc (100 mL)
  3. washThe resulting suspension was washed with water and brine
  4. dry with materialThe combined organic extracts were dried (Na2SO4)
  5. filtrationfiltered
  6. custompurified by silica gel flash chromatography (1:2 EtOAc/hexanes)

Sources & evidence

ORD record
ord-e5c764d122714416998f395d2c662b68
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

Loading…