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

HRID 254306Notes

Reaction equation

HRID 254306 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.[CH3:18][C:19]1(B(O)O)[CH:23]=[C:22]([CH3:24])[O:21][NH:20]1.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>[CH3:18][C:19]1[C:23]([C:2]2[N:6]3[C:7]4[C:12]([N:13]=[C:14]([CH3:15])[C:5]3=[C:4]([CH3:17])[N:3]=2)=[CH:11][CH:10]=[C:9]([F:16])[CH:8]=4)=[C:22]([CH3:24])[O:21][N:20]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 577324521-Bromo-8-fluoro-3,4-dimethylimidazo[1,5-a]quinoxalineHCID 668614323,5-Dimethyl-isoxazoleboronic acid

Product 1

HCID 426294731-(3,5-Dimethylisoxazol-4-yl)-8-fluoro-3,4-dimethylimidazo[1,5-a]quinoxalineYield 77.3%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Following the general Suzuki coupling procedure, reaction of bromide 5A (75 mg, 0.25 mmol), 3,5-dimethylisoxazolboronic acid (178 mg, 1.25 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 (60 mg, 77% yield). EIMS 311.1 [M+H]+.

Sources & evidence

ORD record
ord-0f952c2c175e4884812d0a125d353df7
Source dataset
uspto-grants-2011_01
Patent number
US07875618B2

Reaction notes

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