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Water → 1-p-Tolyl-6-(2-p-tolyl-2H-pyrazol-3-yl)-1H-benzoimidazole

HRID 2202453
Notes
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Reaction equation

HRID 2202453 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:9]=[CH:8][N:7]([C:10]3[CH:15]=[CH:14][C:13]([CH3:16])=[CH:12][CH:11]=3)[C:6]=2[CH:17]=1.[C:18]1([CH3:32])[CH:23]=[CH:22][C:21]([N:24]2[C:28](B(O)O)=[CH:27][CH:26]=[N:25]2)=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+].O>COCCOC.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:13]1([CH3:16])[CH:14]=[CH:15][C:10]([N:7]2[C:6]3[CH:17]=[C:2]([C:28]4[N:24]([C:21]5[CH:22]=[CH:23][C:18]([CH3:32])=[CH:19][CH:20]=5)[N:25]=[CH:26][CH:27]=4)[CH:3]=[CH:4][C:5]=3[N:9]=[CH:8]2)=[CH:11][CH:12]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 962WaterHCID 10340Sodium CarbonateHCID 900950141-p-tolyl-1H-pyrazol-5-ylboronic acid2×HCID 900954586-bromo-1-p-tolyl-1H-benzo[d]imidazole2×

Product 1

HCID 734417941-p-Tolyl-6-(2-p-tolyl-2H-pyrazol-3-yl)-1H-benzoimidazoleYield 43.4%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalyst
HCID 80711,2-DimethoxyethaneSolvent

Procedure

To a mixture of 6-bromo-1-p-tolyl-1H-benzo[d]imidazole (intermediate F) (100 mg, 348 μmol) and 1-p-tolyl-1H-pyrazol-5-ylboronic acid (intermediate B) (91.5 mg, 453 μmol) in 1,2-dimethoxyethane (3 ml) was added 2M sodium carbonate solution (696 μl, 1.39 mmol) and the reaction mixture was purged with argon for 10 min in an ultrasonic bath. To the stirred mixture tetrakis(triphenylphosphine)palladium(0) (80.5 mg, 69.6 μmol) was added at room temperature and the reaction mixture was allowed to stir under reflux conditions for 15 h. The reaction mixture was cooled to room temperature, poured into water (20 ml) and extracted with ethyl acetate (2×20 ml). The combined organic layers were washed with brine (1×20 ml), dried (MgSO4) and evaporated. The crude material (200 mg) was purified by flash chromatography on silica gel (heptane/ethyl acetate 1:1) and trituration from diethyl ether/heptane to yield the title compound as a off-white solid (55 mg, 43%), MS (ISP) m/z=365.2 [(M+H)+], mp 165° C.

Workup

  1. customthe reaction mixture was purged with argon for 10 min in an ultrasonic bath
  2. extractionextracted with ethyl acetate (2×20 ml)
  3. washThe combined organic layers were washed with brine (1×20 ml)
  4. dry with materialdried (MgSO4)
  5. customevaporated
  6. customThe crude material (200 mg) was purified by flash chromatography on silica gel (heptane/ethyl acetate 1:1) and trituration from diethyl ether/heptane

Sources & evidence

ORD record
ord-099f6c61c8d6487bba99abe5fbfcdc87
Source dataset
uspto-grants-2016_06
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US09365550B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes