Potassium Carbonate → HCID 90425944, compound

HRID 2278907Notes

Reaction equation

Cl[C:2]1[CH:7]=[C:6]([O:8][C:9]2[C:10]([CH3:20])=[CH:11][C:12]([NH:16][C:17](=[O:19])[CH3:18])=[N:13][C:14]=2[CH3:15])[CH:5]=[CH:4][N:3]=1.[CH3:21][N:22]1[CH:26]=[C:25](B2OC(C)(C)C(C)(C)O2)[CH:24]=[N:23]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>[CH3:20][C:10]1[C:9]([O:8][C:6]2[CH:5]=[CH:4][N:3]=[C:2]([C:25]3[CH:24]=[N:23][N:22]([CH3:21])[CH:26]=3)[CH:7]=2)=[C:14]([CH3:15])[N:13]=[C:12]([NH:16][C:17](=[O:19])[CH3:18])[CH:11]=1

Participants

Conditions

Temperature: 80 °C

Procedure

A mixture of N-(5-((2-chloropyridin-4-yl)oxy)-4,6-dimethylpyridin-2-yl)acetamide (598 mg, 2.05 mmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (554 mg, 2.66 mmol), K2CO3 (850 mg, 6.15 mmol) and Pd(PPh3)4 (118 mg, 0.102 mmol) in dioxane (8 mL) and water (2 mL) was sparged with Ar and heated at 80° C. overnight. The mixture was cooled to RT, diluted with EtOAc, washed with satd. NaHCO3, then brine, dried over Na2SO4 and concentrated to dryness to afford crude N-(4,6-dimethyl-5-((2-(1-methyl-1H-pyrazol-4-yl)pyridin-4-yl)oxy)pyridin-2-yl)acetamide (100% yield assumed) which was used without further purification. MS (ESI) m/z: 338.1 (M+H+).

Workup

customwas sparged with Ar
temperatureThe mixture was cooled to RT
additiondiluted with EtOAc
washwashed with satd
dry with materialNaHCO3, then brine, dried over Na2SO4
concentrationconcentrated to dryness

Sources & evidence

ORD record: ord-0d28068b72f84b1b843d790e37a70ed9
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09133183B2

Reaction notes

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