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

HRID 706536Notes

Reaction equation

HRID 706536 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>O>[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

6

Reactant 4

HCID 6228DimethylformamideHCID 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 92%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
35 °C

Procedure

A flask was charged with 3-bromo-4-nitro-1H-indazole (64 g, 0.264 mol), 2-(chloromethyl)-6-isopropylpyridine hydrochloride (55 g, 0.264 mol), powdered potassium carbonate (91 g, 0.661 mol), and 500 mL of DMF. This mixture was warmed to 35° C. for 72 hours, then poured into 2 liters of cold water, upon which a tan solid precipitated. After stirring for 20 minutes, the solids were collected by filtration and dried under vacuum to give 91 g (92%) of 3-bromo-1-((6-isopropylpyridin-2-yl)methyl)-4-nitro-1H-indazole.

Workup

  1. customprecipitated
  2. filtrationthe solids were collected by filtration
  3. customdried under vacuum

Sources & evidence

ORD record
ord-1e2a864c99c54d15852079d11ef81b85
Source dataset
uspto-grants-2015_11
Patent number
US09174981B2

Reaction notes

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