Potassium Carbonate → 1-(2,5-Dichlorophenyl)-8-fluoro-3,4-dimethylimidazo[1,5-a]quinoxaline

HRID 254295

Reaction equation

HRID 254295 reaction equation
Br[C:2]1[N:6]2[C:7]3[C:12]([N:13]=[C:14]([CH3:15])[C:5]2=[C:4]([CH3:17])[N:3]=1)=[CH:11][CH:10]=[C:9]([F:16])[CH:8]=3.[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[Cl:18][C:19]1[CH:24]=[CH:23][C:22]([Cl:25])=[CH:21][C:20]=1[C:2]1[N:6]2[C:7]3[C:12]([N:13]=[C:14]([CH3:15])[C:5]2=[C:4]([CH3:17])[N:3]=1)=[CH:11][CH:10]=[C:9]([F:16])[CH:8]=3

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27733712,5-Dichlorobenzeneboronic acidHCID 577324521-Bromo-8-fluoro-3,4-dimethylimidazo[1,5-a]quinoxaline

Product 1

HCID 426292291-(2,5-Dichlorophenyl)-8-fluoro-3,4-dimethylimidazo[1,5-a]quinoxalineYield 25.5%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Following the general Suzuki coupling procedure, reaction of bromide 5A (75 mg, 0.25 mmol), 2,5-dichlorophenylboronic acid (58 mg, 0.30 mmol), K2CO3 (105 mg, 0.75 mmol) and Pd(PPh3)4 (5.8 mg, 0.005 mmol) provided the coupling product as a white powder (23 mg, 25% yield). EIMS 360.0 [M+H]+.

Sources & evidence

ORD record
ord-7033932dd6734dde86e28b79a08a123c
Source dataset
uspto-grants-2011_01
Patent number
US07875618B2

Linked notes

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