Potassium Carbonate → HCID 90402579, compound

HRID 1049258Notes

Reaction equation

[CH3:1][N:2]1[CH:6]=[C:5](B2OC(C)(C)C(C)(C)O2)[CH:4]=[N:3]1.Cl[C:17]1[CH:22]=[C:21]([O:23][C:24]2[C:25]([CH3:34])=[N:26][C:27]([N+:31]([O-:33])=[O:32])=[CH:28][C:29]=2[CH3:30])[CH:20]=[CH:19][N:18]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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>[CH3:34][C:25]1[C:24]([O:23][C:21]2[CH:22]=[CH:17][N:18]=[C:19]([C:5]3[CH:4]=[N:3][N:2]([CH3:1])[CH:6]=3)[CH:20]=2)=[C:29]([CH3:30])[CH:28]=[C:27]([N+:31]([O-:33])=[O:32])[N:26]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (237 mg, 1.139 mmol), 3-((2-chloropyridin-4-yl)oxy)-2,4-dimethyl-6-nitropyridine (245 mg, 0.876 mmol), K2CO3 (363 mg, 2.63 mmol) and Pd(PPh3)4 (51 mg, 0.044 mmol) in dioxane (4 mL) and water (1 mL) was sparged with Ar, heated at 80° C. for 24 h, then cooled to RT. The mixture was diluted with EtOAc. Washed with satd. NaHCO3, then brine, dried over Na2SO4 and concentrated to dryness to afford 2,4-dimethyl-3-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)-6-nitropyridine (100% yield assumed) which was used without further purification. MS (ESI) m/z: 326.1 (M+H+).

Workup

customwas sparged with Ar
temperaturecooled to RT
additionThe mixture was diluted with EtOAc
washWashed with satd
dry with materialNaHCO3, then brine, dried over Na2SO4
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-0f59af2c880549f6ba97617716bd4808
Source dataset: uspto-grants-2016_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09382228B2

Reaction notes

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