Potassium Carbonate → HCID 57799434, compound

HRID 2101365Notes

Reaction equation

Br[C:2]1[CH:7]=[CH:6][N:5]2[C:8](=[O:15])[N:9]([CH2:11][CH:12]([CH3:14])[CH3:13])[N:10]=[C:4]2[C:3]=1[C:16]1[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][CH:17]=1.[C:23]([O-:26])([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>[Cl:22][C:19]1[CH:20]=[CH:21][C:16]([C:3]2[C:4]3[N:5]([C:8](=[O:15])[N:9]([CH2:11][CH:12]([CH3:14])[CH3:13])[N:10]=3)[CH:6]=[CH:7][C:2]=2[C:3]2[CH:4]=[N:5][C:6]([O:26][CH3:23])=[CH:7][CH:2]=2)=[CH:17][CH:18]=1

Participants

Conditions

Temperature: 150 °C

Procedure

To a stirring, degassed mixture of 7-bromo-8-(4-chlorophenyl)-2-isobutyl-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (0.05 g, 0.13 mmol), 2-methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaboralan-2-yl)pyridine (0.09 g, 0.39 mmol), and tetrakis(triphenylphosphine)palladium (8 mg, 0.007 mmol) in dioxane (1.0 mL) at 20° C. was added K2CO3 (0.04 g, 0.26 mmol) in water (0.34 mL). The resulting reaction mixture was heated in a microwave reactor at 150° C. for 10 min under argon. Analysis by HPLC/MS indicated that starting material had been consumed. The reaction mixture was brought to room temperature and was concentrated under reduced pressure. The crude product was purified by reverse phase preparative HPLC (acetonitrile-water-TFA) to isolate 27 mg of the title compound as a yellow solid. MS: [M+H]+=409.

Workup

customTo a stirring, degassed
customThe resulting reaction mixture
customhad been consumed
customwas brought to room temperature
concentrationwas concentrated under reduced pressure
customThe crude product was purified by reverse phase preparative HPLC (acetonitrile-water-TFA)

Sources & evidence

ORD record: ord-ae6c002cd6464b0190946e2e44dcec93
Source dataset: uspto-grants-2009_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07572808B2

Reaction notes

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