Potassium Carbonate → HCID 90402579, compound

HRID 718186Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:19])=[N:11][C:12]([N+:16]([O-:18])=[O:17])=[CH:13][C:14]=2[CH3:15])[CH:5]=[CH:4][N:3]=1.[CH3:20][N:21]1[CH:25]=[C:24](B2OC(C)(C)C(C)(C)O2)[CH:23]=[N:22]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>[CH3:19][C:10]1[C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:24]3[CH:23]=[N:22][N:21]([CH3:20])[CH:25]=3)[CH:7]=2)=[C:14]([CH3:15])[CH:13]=[C:12]([N+:16]([O-:18])=[O:17])[N:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

3((2-Chloropyridin-4-yl)oxy)-2,4-dimethyl-6-nitropyridine (0.50 g, 1.8 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (0.48 g, 2.3 mmol), and K2CO3 (0.37 g, 2.7 mmol) were suspended in dioxane (6 mL) and water (1.2 mL) and sonicated and sparged with Ar for 10 min. Pd(PPh3)4 (0.10 g, 0.089 mmol) was added and the reaction mixture was stirred at 80° C. for 12 h. The mixture was diluted with water (20 mL) and extracted with EtOAc (4×25 mL). The combined organics were dried and concentrated in vacuo. The residue was purified by silica gel chromatography (MeOH/DCM) to afford 2,4-dimethyl-3-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)-6-nitropyridine (0.56 g, 96%) as a brown oil. MS (ESI) m/z: 326.1 (M+H+).

Workup

customsparged with Ar for 10 min
extractionextracted with EtOAc (4×25 mL)
customThe combined organics were dried
concentrationconcentrated in vacuo
customThe residue was purified by silica gel chromatography (MeOH/DCM)

Sources & evidence

ORD record: ord-ce1dea330d9d453d991e3bb64e1cdb4c
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193719B2

Reaction notes

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