Potassium Carbonate → 4-Fluoro-3-(6-fluoro-8-methoxy-3,4-dimethylimidazo[1,5-a]quinoxalin-1-yl)benzamide

HRID 254310Notes

Reaction equation

HRID 254310 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.[F:20][C:21]1[CH:26]=[CH:25][C:24]([C:27](=[O:29])[NH2:28])=[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:20][C:21]1[CH:26]=[CH:25][C:24]([C:27]([NH2:28])=[O:29])=[CH:23][C:22]=1[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

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 447174785-Carbamoyl-2-fluorobenzeneboronic acidHCID 577324641-Bromo-6-fluoro-8-methoxy-3,4-dimethylimidazo[1,5-a]quinoxaline

Product 1

HCID 426294774-Fluoro-3-(6-fluoro-8-methoxy-3,4-dimethylimidazo[1,5-a]quinoxalin-1-yl)benzamideYield 11%

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-fluoro-5-carbamoylphenylboronic acid (55 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 (8 mg, 11% yield). EIMS 383.1 [M+H]+.

Sources & evidence

ORD record
ord-ccfe02dde21d4dbea34580a3cb1861a0
Source dataset
uspto-grants-2011_01
Patent number
US07875618B2

Reaction notes

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