Potassium tert-butoxide → tert-butyl 3-bromo-10,11-dihydropyrazino [1',2':1,2]imidazo[4,5-c]quinohne-9(8H)-carboxylate

HRID 1364055Notes

Reaction equation

HRID 1364055 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]2[C:6]3[N:14]([CH2:15][CH2:16][NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[C:13]([CH2:25]Cl)=[N:12][C:7]=3[CH:8]=[N:9][C:10]=2[CH:11]=1.CC(C)([O-])C.[K+]>C1COCC1>[Br:1][C:2]1[CH:11]=[C:10]2[C:5]([C:6]3[N:14]4[CH2:15][CH2:16][N:17]([C:18]([O:19][C:20]([CH3:23])([CH3:22])[CH3:21])=[O:24])[CH2:25][C:13]4=[N:12][C:7]=3[CH:8]=[N:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 23665647Potassium tert-butoxideHCID 66958693HCID 66958693, compound

Product 1

HCID 131728692tert-butyl 3-bromo-10,11-dihydropyrazino [1',2':1,2]imidazo[4,5-c]quinohne-9(8H)-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The method described in Part D of Example 365 was used to treat tert-butyl 2-[7-bromo-2-(chloromethyl)-1H-imidazo[4,5-c]quinolin-1-yl]ethylcarbamate (10.0 g, 22.7 mmol) with potassium tert-butoxide (27.29 mL of a 1 M solution in THF) with the modification that the reaction was stirred overnight to provide tert-butyl 3-bromo-10,11-dihydropyrazino [1′,2′:1,2]imidazo[4,5-c]quinohne-9(8H)-carboxylate in a crude mixture.

Sources & evidence

ORD record
ord-16975525f0f04ec8875b77439612534f
Source dataset
uspto-grants-2011_02
Patent number
US07888349B2

Reaction notes

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