Ethyl Acetate → 2-Ethyl-3-[[2-(1-methyl-1h-pyrazol-4-yl)-4-pyridinyl]oxy]-6-nitropyridine

HRID 718175Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH2:18][CH3:19])=[N:11][C:12]([N+:15]([O-:17])=[O:16])=[CH:13][CH:14]=2)[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+].CCOC(C)=O>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>[CH2:18]([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)=[CH:14][CH:13]=[C:12]([N+:15]([O-:17])=[O:16])[N:11]=1)[CH3:19]

Participants

Conditions

Temperature: 80 °C

Procedure

3-((2-chloropyridin-4-yl)oxy)-2-ethyl-6-nitropyridine (1.0 g, 3.6 mmol) and 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (1.0 g, 4.6 mmol) were dissolved in dioxane (10 mL). A solution of K2CO3 (1.5 g, 10.6 mmol) in water (2 mL) was added and the mixture was sonicated and sparged with Ar for 10 min. Pd(PPh3)4 (0.21 g, 0.18 mmol) was added and the reaction mixture was stirred at 80° C. for 24 h. EtOAc (60 mL) was added and the mixture was washed with sat. NaHCO3 (aq) (60 mL) and brine (60 mL), dried (Na2SO4), and concentrated in vacuo to afford 2-ethyl-3-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)-6-nitropyridine (1.2 g, 100%) as a brown viscous oil that was carried forward without further purification. MS (ESI) m/z: 326.1 (M+H+).

Workup

customthe mixture was sonicated
customsparged with Ar for 10 min
washthe mixture was washed with sat. NaHCO3 (aq) (60 mL) and brine (60 mL)
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo

Sources & evidence

ORD record: ord-b84a06c9186246de9ce80d8f05923dd7
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09193719B2

Reaction notes

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