Potassium Carbonate → 3-iodo-1-((1-(4-methoxybenzyl)-1H-pyrazol-5-yl)methyl)-4-nitro-1H-indazole

HRID 79340Notes

Reaction equation

HRID 79340 reaction equation
[I: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.Br[CH2:15][C:16]1[N:20]([CH2:21][C:22]2[CH:27]=[CH:26][C:25]([O:28][CH3:29])=[CH:24][CH:23]=2)[N:19]=[CH:18][CH:17]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.CCOC(C)=O>[I: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]([CH2:15][C:16]2[N:20]([CH2:21][C:22]3[CH:23]=[CH:24][C:25]([O:28][CH3:29])=[CH:26][CH:27]=3)[N:19]=[CH:18][CH:17]=2)[N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 672614135-(bromomethyl)-1-(4-methoxybenzyl)-1H-pyrazoleHCID 178526562HCID 178526562, compound

Product 1

HCID 672610463-iodo-1-((1-(4-methoxybenzyl)-1H-pyrazol-5-yl)methyl)-4-nitro-1H-indazoleYield 89.4%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 3-iodo-4-nitro-1H-indazole (1.55 g, 5.37 mmol) in DMF (20 mL) was added 5-(bromomethyl)-1-(4-methoxybenzyl)-1H-pyrazole (1.51 g, 5.37 mmol) and K2CO3 (1.11 g, 8.06 mmol). The reaction mixture was stirred overnight, diluted with EtOAc (100 mL), washed with H2O and brine (10 mL), and then concentrated under reduced pressure. Silica gel chromatography (Hexanes/EtOAc 5:1) provided the desired product (2.35 g).

Workup

  1. washwashed with H2O and brine (10 mL)
  2. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-315d07067760471fb7d6f5768a2b2ab6
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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