Bromomethyl 4-methoxyphenyl ketone → 5-Amino-2-(1-[4-methoxyphenylcarbonylmethyl]benzimidazol-2-yl)-pyrazole

HRID 30506

Reaction equation

HRID 30506 reaction equation
[NH2:1][C:2]1[CH:3]=[CH:4][N:5]([C:7]2[NH:11][C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=2)[N:6]=1.[CH3:16][O:17][C:18]1[CH:27]=[CH:26][C:21]([C:22](=[O:25])[CH2:23]Br)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[K+].[K+]>O>[NH2:1][C:2]1[CH:3]=[CH:4][N:5]([C:7]2[N:11]([CH2:23][C:22]([C:21]3[CH:26]=[CH:27][C:18]([O:17][CH3:16])=[CH:19][CH:20]=3)=[O:25])[C:10]3[CH:12]=[CH:13][CH:14]=[CH:15][C:9]=3[N:8]=2)[N:6]=1

Participants

5

Reactant 3

HCID 4965Bromomethyl 4-methoxyphenyl ketoneHCID 11430Potassium CarbonateHCID 574644725-amino-2-(1H-benzimidazol-2-yl)pyrazole

Product 1

HCID 574943345-Amino-2-(1-[4-methoxyphenylcarbonylmethyl]benzimidazol-2-yl)-pyrazole

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A suspension of 5-amino-2-(1H-benzimidazol-2-yl)pyrazole (0.10 g, 0.5 mmol), p-methoxyphenacyl bromide (0.204 g, 0.9 mmol) and dry potassium carbonate (0.173 g, 1.25 mmol) is stirred at room temperature for 16 hours. The mixture is diluted with water and the product extracted with ethyl acetate. The product is purified by chromatography on silicagel. M.p. 136-140° C., 1H-NMR (400 MHz, d6-DMSO): 8.04 (d, 2H); 7.58 (m, 2H); 7.28 (m, 3H); 7.11 (d, 2H); 6.84 (s, 2H); 6.26 (s, 2H); 5.39 (d, 1H); 3.87 (s, 3H).

Workup

  1. extractionthe product extracted with ethyl acetate
  2. customThe product is purified by chromatography on silicagel

Sources & evidence

ORD record
ord-f8b0f03890c64aedba67ef2fd6510344
Source dataset
uspto-grants-2008_09
Patent number
US07423157B2

Linked notes

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