Potassium Carbonate → 6-Fluoro-8-methoxy-3,4-dimethyl-1-(2-methylphenyl)-imidazo[1,5-a]quinoxaline

HRID 254307Notes

Reaction equation

HRID 254307 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]([CH3:19])[N:3]=1)=[C:11]([F:16])[CH:10]=[C:9]([O:17][CH3:18])[CH:8]=3.[CH3:20][C:21]1[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=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>[F:16][C:11]1[CH:10]=[C:9]([O:17][CH3:18])[CH:8]=[C:7]2[C:12]=1[N:13]=[C:14]([CH3:15])[C:5]1[N:6]2[C:2]([C:22]2[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=2[CH3:20])=[N:3][C:4]=1[CH3:19]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27332672-Methylphenyl boronic acidHCID 577324641-Bromo-6-fluoro-8-methoxy-3,4-dimethylimidazo[1,5-a]quinoxaline

Product 1

HCID 426294746-Fluoro-8-methoxy-3,4-dimethyl-1-(2-methylphenyl)-imidazo[1,5-a]quinoxalineYield 30%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Following the general Suzuki coupling procedure, reaction of bromide 6A (65 mg, 0.2 mmol), 2-methylphenylboronic acid (40 mg, 0.3 mmol), K2CO3 (82 mg, 0.6 mmol) and Pd(PPh3)4 (5 mg, 0.004 mmol) provided the coupling product as an off-white powder (20 mg, 30% yield). EIMS 336.1 [M+H]+.

Sources & evidence

ORD record
ord-ab5076b76cd24eb692ece05408fcc402
Source dataset
uspto-grants-2011_01
Patent number
US07875618B2

Reaction notes

Loading…