Sodium Hydroxide → 2-Amino-1-[3-(1,3,5-trimethyl-4-pyrazolyl)phenyl]benzimidazole

HRID 413740Notes

Reaction equation

HRID 413740 reaction equation
[NH2:1][C:2]1[N:6]([C:7]2[CH:8]=[C:9](B3OCCCO3)[CH:10]=[CH:11][CH:12]=2)[C:5]2[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=2[N:3]=1.Br[C:24]1[C:25]([CH3:31])=[N:26][N:27]([CH3:30])[C:28]=1[CH3:29].C(=O)([O-])O.[Na+].[OH-].[Na+]>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.COCCOC.O>[NH2:1][C:2]1[N:6]([C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([C:24]3[C:25]([CH3:31])=[N:26][N:27]([CH3:30])[C:28]=3[CH3:29])[CH:8]=2)[C:5]2[CH:19]=[CH:20][CH:21]=[CH:22][C:4]=2[N:3]=1

Participants

8

Reactant 4

HCID 14798Sodium HydroxideHCID 516892Sodium BicarbonateHCID 5191814-Bromo-1,3,5-trimethylpyrazoleHCID 18522055HCID 18522055, compound

Product 1

HCID 185220732-Amino-1-[3-(1,3,5-trimethyl-4-pyrazolyl)phenyl]benzimidazole

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

A mixture of 2-(3-(2-amino-1-benzimidazolyl)phenyl)-1,3,2-dioxaborinane (2.0 g, 6.82 mmol), 4-bromo-1,3,5-trimethylpyrazole (1.29 g, 6.82 mmol), tetrakis(triphenylphosphine)-palladium(0) (0.24 g, 0.20 mmol), sodium hydrogen carbonate (2.29 g, 27.3 mmol), water (27 ml) and 1,2-dimethoxyethane (54 ml) was stirred at reflux overnight. Aqueous sodium hydroxide (50 ml) was added and the mixture was extracted twice with ethyl acetate (50 ml). The crude extract was purified by chromatography using silica gel and a mixture of ethanol (4%) and dichloromethane as eluent. The product was isolated as the free base. Yield 0.60 g, 28%. M.p. 198-200° C.

Workup

  1. temperatureat reflux overnight
  2. extractionthe mixture was extracted twice with ethyl acetate (50 ml)
  3. extractionThe crude extract
  4. customwas purified by chromatography
  5. additiona mixture of ethanol (4%) and dichloromethane as eluent
  6. customThe product was isolated as the free base

Sources & evidence

ORD record
ord-010dcf7ef7254ae086bcc83cb4b35bfe
Source dataset
uspto-grants-2003_05
Patent number
US06569880B2

Reaction notes

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