Triethylamine → HCID 67746822, compound

HRID 375531Notes

Reaction equation

HRID 375531 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([C:8]2[NH:12][C:11]3[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=3[N:9]=2)=[CH:4][CH:3]=1.[CH2:17]([N:21]1[CH2:26][CH2:25][N:24]([C:27]2[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=2)[CH2:23][CH2:22]1)[CH2:18][CH:19]=[CH2:20].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CC)CC)C>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[NH3:9].[C:27]1([N:24]2[CH2:23][CH2:22][N:21]([CH2:17][CH2:18]/[CH:19]=[CH:20]\[C:2]3[CH:7]=[CH:6][C:5]([C:8]4[NH:12][C:11]5[CH:13]=[CH:14][CH:15]=[CH:16][C:10]=5[N:9]=4)=[CH:4][CH:3]=3)[CH2:26][CH2:25]2)[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

8

Reactant 4

HCID 8471TriethylamineHCID 80271Tri-o-tolylphosphineHCID 2861822-(4-Bromophenyl)benzimidazoleHCID 18993040HCID 18993040, compound

Product 2

HCID 222AmmoniaHCID 67746822HCID 67746822, compoundYield 30.4%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

A mixture of 2-(4-bromophenyl)-1H-benzimidazole (Example F) (8.08 g), 1-but-3-enyl-4-phenylpiperazine (Example G) (8.0 g), palladium acetate (0.66 g), tri-o-tolylphosphine (1.8 g) and triethylamine (7.05 g) in acetonitrile (100 mL) is stirred at reflux for 2 hours. The mixture is cooled and filtered through Celite. The filtrate is evaporated to leave a brown solid. This solid is purified by MPLC on silica gel eluting with 100:8:1 dichloromethane: ethanol: 0.880 aqueous ammonia to give 1.84 g of the title compound as a white solid; mp 140°-145° C.

Workup

  1. temperatureat reflux for 2 hours
  2. temperatureThe mixture is cooled
  3. filtrationfiltered through Celite
  4. customThe filtrate is evaporated
  5. customto leave a brown solid
  6. customThis solid is purified by MPLC on silica gel eluting with 100:8:1 dichloromethane

Sources & evidence

ORD record
ord-58e9532f1c9a4e5fb612bfaaf26b7ec6
Source dataset
uspto-grants-1996_01
Patent number
US05486517

Reaction notes

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