Potassium Carbonate → 3-(1-(3,5-Dimethoxy-2-nitrophenyl)-4-methyl-1H-imidazol-2-yl)-4-methylpyridine

HRID 254324Notes

Reaction equation

HRID 254324 reaction equation
Br[C:2]1[N:3]([C:8]2[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=[C:10]([O:16][CH3:17])[C:9]=2[N+:18]([O-:20])=[O:19])[CH:4]=[C:5]([CH3:7])[N:6]=1.[CH3:21][C:22]1[CH:27]=[CH:26][N:25]=[CH:24][C:23]=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>[CH3:17][O:16][C:10]1[C:9]([N+:18]([O-:20])=[O:19])=[C:8]([N:3]2[CH:4]=[C:5]([CH3:7])[N:6]=[C:2]2[C:23]2[CH:24]=[N:25][CH:26]=[CH:27][C:22]=2[CH3:21])[CH:13]=[C:12]([O:14][CH3:15])[CH:11]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27627114-Methylpyridine-3-Boronic AcidHCID 566484922-bromo-1-(3,5-dimethoxy-2-nitrophenyl)-4-methyl-1H-imidazole

Product 1

HCID 577324553-(1-(3,5-Dimethoxy-2-nitrophenyl)-4-methyl-1H-imidazol-2-yl)-4-methylpyridineYield 69.5%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Procedure

Following the general Suzuki coupling procedure, reaction of 2-bromo-1-(3,5-dimethoxy-2-nitrophenyl)-4-methyl-1H-imidazole (1.1 g, 3.2 mmol), 4-methyl-3-pyridylboronic acid (876 mg, 6.4 mmol), K2CO3 (1.32 g, 9.6 mmol) and Pd(PPh3)4 (186 mg, 0.161 mmol) provided 788 mg (69% yield) of the desired product as an off white powder. EIMS 355.1 [M+H]+.

Sources & evidence

ORD record
ord-735341ffa61e440a8be8b7ec0e979389
Source dataset
uspto-grants-2011_01
Patent number
US07875618B2

Reaction notes

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