Water → 3-(4-Aminophenyl)-5-(1-methyl-1H-pyrazol-4-yl)pyridin-2-amine

HRID 1428111Notes

Reaction equation

O.C(=O)([O-])[O-].[K+].[K+].[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([NH2:22])=[N:17][CH:18]=[C:19](Br)[CH:20]=2)=[CH:11][CH:10]=1.[CH3:23][N:24]1[CH:28]=[C:27](B2OC(C)(C)C(C)(C)O2)[CH:26]=[N:25]1>O1CCOCC1.C(Cl)(Cl)Cl.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>[NH2:8][C:9]1[CH:14]=[CH:13][C:12]([C:15]2[C:16]([NH2:22])=[N:17][CH:18]=[C:19]([C:27]3[CH:26]=[N:25][N:24]([CH3:23])[CH:28]=3)[CH:20]=2)=[CH:11][CH:10]=1

Participants

Conditions

Temperature: 100 °C

Procedure

Water (5 ml), potassium carbonate (1742 mg) and tetrakis(triphenylphosphine)palladium (242 mg) were added to a solution of the compound obtained in Step 1 of Example 1 (1110 mg) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (874 mg) in 1,4-dioxane (50 ml), and the mixture was stirred at 100° C. for five hours. After leaving to cool, the reaction solution was diluted with chloroform. The organic layer was washed with water and brine and dried over sodium sulfate. The solvent was distilled off under reduced pressure, and the residue was purified by silica gel column chromatography [chloroform:methanol=96:4 (v/v)] to give 638 mg of the title compound as a solid.

Workup

customAfter leaving
temperatureto cool
washThe organic layer was washed with water and brine
dry with materialdried over sodium sulfate
distillationThe solvent was distilled off under reduced pressure
customthe residue was purified by silica gel column chromatography [chloroform:methanol=96:4 (v/v)]

Sources & evidence

ORD record: ord-e137cd6a2e4146a59f6aa467d85ab756
Source dataset: uspto-grants-2015_01
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08933103B2

Reaction notes

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