Potassium Carbonate → 3-iodo-1-((2-methoxy-6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazole

HRID 79362Notes

Reaction equation

HRID 79362 reaction equation
Br[CH2:2][C:3]1[C:4]([O:10][CH3:11])=[N:5][C:6]([CH3:9])=[CH:7][CH:8]=1.[I:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[N+:22]([O-:24])=[O:23])[NH:15][N:14]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[I:12][C:13]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[N+:22]([O-:24])=[O:23])[N:15]([CH2:2][C:3]2[C:4]([O:10][CH3:11])=[N:5][C:6]([CH3:9])=[CH:7][CH:8]=2)[N:14]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 672536903-(Bromomethyl)-2-methoxy-6-methylpyridineHCID 178526562HCID 178526562, compound

Product 1

HCID 672596093-iodo-1-((2-methoxy-6-methylpyridin-3-yl)methyl)-4-nitro-1H-indazoleYield 101.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 3-(bromomethyl)-2-methoxy-6-methylpyridine (500 mg, 2.314 mmol) and 3-iodo-4-nitro-1H-indazole (668.8 mg, 2.314 mmol) in DMF (10 mL) was added K2CO3 (479.7 mg, 3.471 mmol). The reaction mixture was stirred at ambient temperature for 16 hours. The reaction mixture was diluted with EtOAc, washed with water, brine and concentrated under reduced pressure to give the product (1.0 g).

Workup

  1. washwashed with water, brine
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-334da8b6c370411392bb7b956942d6fc
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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