1,4-Dibromobutane → 5H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine

HRID 1290745Notes

Reaction equation

HRID 1290745 reaction equation
[CH:1]1[N:5]2[C:6]3[CH2:17][C:16]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[C:7]=3[NH:8][C:9](=O)[C:4]2=[N:3][CH:2]=1.[OH-].[Na+].BrCCCCBr>[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.CS(C)=O>[CH2:1]1[N:5]2[C:6]3[CH2:17][C:16]4[CH:15]=[CH:14][CH:13]=[CH:12][C:11]=4[C:7]=3[NH:8][CH:9]=[C:4]2[N:3]=[CH:2]1

Participants

6

Reactant 3

HCID 80561,4-DibromobutaneHCID 14798Sodium HydroxideHCID 103535495H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazin-4-one

Product 1

HCID 1317206565H,10H-imidazo[1,2-a]indeno[1,2-e]pyrazine

Reagents, catalysts & solvents 2

HCID 74236Tetrabutylammonium BromideCatalystHCID 679Dimethyl SulfoxideSolvent

Procedure

The procedure is performed as in Example 9, but starting with 1.1 g of 5H,10H-imidazo[1,2-a]indeno-[1,2-e]pyrazin-4-one, 40 ml of dimethyl sulphoxide, 2 g of sodium hydroxide pellets, 32 mg of tetrabutylammonium bromide and 0.6 ml of 1,4-dibromobutane. After drying at 80° C., 0.17 g of spiro[5H,10H-imidazo[1,2-a]indeno[l,2-e]pyrazine-10:1'-cyclopentane]-4-one is obtained, in the form of a white solid melting above 260° C. (Analysis % calculated C: 73.63, H: 5.45, N: 15.15, O: 5.77, % found C: 73.8, H: 5.8, N: 15.1, O: 6.0).

Workup

  1. customAfter drying at 80° C.

Sources & evidence

ORD record
ord-dbf8d9ad7a874a66bfbc50ff6bbc3020
Source dataset
uspto-grants-1998_05
Patent number
US05753657

Reaction notes

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