Triethylamine → 5-([1,1'-Biphenyl]-4-ylcarbonyl)-4,5-dihydropyrrolo[1,2-a]quinoxaline

HRID 1956349Notes

Reaction equation

HRID 1956349 reaction equation
[CH:1]1[N:5]2[C:6]3[C:11]([NH:12][CH2:13][C:4]2=[CH:3][CH:2]=1)=[CH:10][CH:9]=[CH:8][CH:7]=3.[C:14]1([C:23]2[CH:28]=[CH:27][CH:26]=[CH:25][CH:24]=2)[CH:19]=[CH:18][C:17]([C:20](Cl)=[O:21])=[CH:16][CH:15]=1.C(N(CC)CC)C>C(Cl)Cl.C(Cl)(Cl)Cl>[C:14]1([C:23]2[CH:24]=[CH:25][CH:26]=[CH:27][CH:28]=2)[CH:15]=[CH:16][C:17]([C:20]([N:12]2[C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[N:5]3[CH:1]=[CH:2][CH:3]=[C:4]3[CH2:13]2)=[O:21])=[CH:18][CH:19]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 841514-Phenylbenzoyl chlorideHCID 118051814,5-Dihydropyrrolo[1,2-a]quinoxaline

Product 1

HCID 110681015-([1,1'-Biphenyl]-4-ylcarbonyl)-4,5-dihydropyrrolo[1,2-a]quinoxalineYield 84.5%

Reagents, catalysts & solvents 2

HCID 6212ChloroformSolventHCID 6344DichloromethaneSolvent

Procedure

To a mixture of 0.5 g of 4,5-dihydropyrrolo[1,2-a]quinoxaline and 0.96 g of 4-biphenylcarbonyl chloride in 50 ml of methylene chloride under argon is added 7.0 ml of triethylamine followed by stirring at room temperature for 16 hours. The reaction mixture is diluted with 50 ml of chloroform and washed with water, 2N HCl, saturated NaHCO3 and water. The organic layer is dried (Na2SO4) and columned on silica gel by elution with 7:1 to 1:1 ethyl acetate:hexane to give 0.87 g of the desired product as a solid. M+H 351.2; M+Na 373.2.

Workup

  1. washwashed with water, 2N HCl, saturated NaHCO3 and water
  2. dry with materialThe organic layer is dried (Na2SO4)
  3. washcolumned on silica gel by elution with 7:1 to 1:1 ethyl acetate

Sources & evidence

ORD record
ord-a701fb4fc8fd4e9aa95388068e2e7c85
Source dataset
uspto-grants-1998_07
Patent number
US05780471

Reaction notes

Loading…