Potassium Carbonate → 5-(4-Fluorophenyl)-N-methylimidazo[1,2-a]pyrazin-8-amine

HRID 1371374Notes

Reaction equation

HRID 1371374 reaction equation
Br[C:2]1[N:7]2[CH:8]=[CH:9][N:10]=[C:6]2[C:5]([NH:11][CH3:12])=[N:4][CH:3]=1.[F:13][C:14]1[CH:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C([O-])([O-])=O.[K+].[K+]>CN(C=O)C.O.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:13][C:14]1[CH:19]=[CH:18][C:17]([C:2]2[N:7]3[CH:8]=[CH:9][N:10]=[C:6]3[C:5]([NH:11][CH3:12])=[N:4][CH:3]=2)=[CH:16][CH:15]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 2856454-Fluorophenylboronic acidHCID 587777925-Bromo-N-methylimidazo[1,2-a]pyrazin-8-amine2×

Product 1

HCID 587778065-(4-Fluorophenyl)-N-methylimidazo[1,2-a]pyrazin-8-amine

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
170 °C

Procedure

To a solution of (5-bromo-imidazo[1,2-a]pyrazin-8-yl)-methyl-amine (intermediate O) (68 mg, 0.3 mmol) in DMF (4 ml) and water (2 ml) was added 4-fluorobenzene boronic acid (84 mg, 0.6 mmol), K2CO3 (165 mg 1.2 mmol), and Pd(PPh3)4 (35 mg, 0.1 eq). The mixture was heated at 170° C. in microwave for 6 min. The mixture was purified on a silica gel column to give the title compound.

Workup

  1. customThe mixture was purified on a silica gel column

Sources & evidence

ORD record
ord-56257f0a17d14d549853927ff4489013
Source dataset
uspto-grants-2007_01
Patent number
US07157460B2

Reaction notes

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