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

HRID 79311Notes

Reaction equation

HRID 79311 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.Cl.Cl[CH2:16][C:17]1[CH:18]=[N:19][N:20]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[CH:21]=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]([CH2:16][C:17]2[CH:18]=[N:19][N:20]([CH2:22][C:23]3[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=3)[CH:21]=2)[N:3]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 67259699HCID 67259699, compoundHCID 178526562HCID 178526562, compound

Product 1

HCID 672616463-iodo-1-((1-(4-methoxybenzyl)-1H-pyrazol-4-yl)methyl)-4-nitro-1H-indazoleYield 79.9%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To 3-iodo-4-nitro-1H-indazole (2.13 g, 7.37 mmol) in DMF (20 mL) was added 4-(chloromethyl)-1-(4-methoxybenzyl)-1H-pyrazole hydrochloride (2.21 g, 8.11 mmol) and K2CO3 (3.06 g, 22.1 mmol). The reaction mixture was stirred for 16 hours. The reaction mixture was diluted with EtOAc, washed with H2O, and brine, and the filtrate was concentrated under reduced pressure. Silica gel chromatography (hexanes/EtOAc 5:1) provided the desired product (2.88 g).

Workup

  1. washwashed with H2O, and brine
  2. concentrationthe filtrate was concentrated under reduced pressure

Sources & evidence

ORD record
ord-4939bdb5d3534aa68afa6ca7fe165388
Source dataset
uspto-grants-2014_09
Patent number
US08841455B2

Reaction notes

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