Potassium Carbonate → HCID 19426025, compound

HRID 742374Notes

Reaction equation

HRID 742374 reaction equation
[CH3:1][N:2]1[CH2:13][C:5]2[CH:6]=[CH:7][C:8]3[C:12]([C:4]=2[CH2:3]1)=[N:11][CH2:10][N:9]=3.C([O-])([O-])=O.[K+].[K+].[Br:20][C:21]1[CH:22]=[C:23](I)[CH:24]=[CH:25][CH:26]=1>CN1CCCC1=O.[Cu]>[Br:20][C:21]1[CH:26]=[C:25]([N:9]2[C:8]3[CH:7]=[CH:6][C:5]4[CH2:13][N:2]([CH3:1])[CH2:3][C:4]=4[C:12]=3[NH:11][CH2:10]2)[CH:24]=[CH:23][CH:22]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 11561Benzene, 1-bromo-3-iodo-HCID 19425983HCID 19425983, compound

Product 1

HCID 19426025HCID 19426025, compound

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Procedure

A mixture of 6,8-dihydro-7-methyl-2H-pyrrolo[3,4-e]benzimidazole (0.25 g), K2CO3 (0.26 g), 3-bromo-1-iodobenzene (0.8 g) and Copper powder (15-20 mg) was heated in N-methyl-2-pyrrolidone (5 ml) at 180° C. for 3 hours. The mixture was then partitioned between EtOAc and water. The organic phase was dried over Na2SO4 and evaporated. The oily residue was purified on SiO2 with EtOAc as the eluent. 1H--NMR (500MHz,CDCl3) ppm: 2.8(s,3H), 4.2(s,2H), 4.45(s,2H), 7.2-7.7(m,6H aromatic) 8.1 (s, 1H imidazole).

Workup

  1. customThe mixture was then partitioned between EtOAc and water
  2. dry with materialThe organic phase was dried over Na2SO4
  3. customevaporated
  4. customThe oily residue was purified on SiO2 with EtOAc as the eluent

Sources & evidence

ORD record
ord-267d67f3fb11461691b499c5348624f0
Source dataset
uspto-grants-1996_09
Patent number
US05554632

Reaction notes

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