[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[NH:7][C:6]3[CH2:11][N:12]([CH:14]([CH3:16])[CH3:15])[CH2:13][C:5]=3[C:4]=2[CH:3]=1.Br[C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.C(=O)([O-])[O-].[Na+].[Na+]>CN1CCCC1=O>[ClH:1].[Cl:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([C:18]3[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=3)[C:6]3[CH2:11][N:12]([CH:14]([CH3:16])[CH3:15])[CH2:13][C:5]=3[C:4]=2[CH:3]=1A mixture of 7.8 g. (33.2 m moles) of 7-chloro-2-i-propyl-1,2,3,4-tetrahydropyrrolo[3,4-b]indole, 18.23 g. (0.116 mole) of bromobenzene, 10.4 g. (0.0364 mole) of cuprous bromide and 4.51 g. (0.0364 mole) sodium carbonate in 125 ml. of N-methyl-2-pyrrolidinone is heated under a nitrogen atmosphere at an internal temperature of 184° C. for 9 hrs. The mixture is cooled, decanted into 300 ml. of water containing 30 ml. of ethylene diamine and sodium chloride and extracted with benzene. The combined extracts are back-washed with a saturated brine solution, dried over magnesium sulfate and concentrated in vacuo.
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