Potassium Carbonate → HCID 58044589, compound

HRID 2368018Notes

Reaction equation

HRID 2368018 reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]2[N:6]([C:8](=[O:11])[NH:9][N:10]=2)[CH:7]=1.[F:12][C:13]([F:25])([F:24])[O:14][C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1.C(=O)([O-])[O-].[K+].[K+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[F:12][C:13]([F:24])([F:25])[O:14][C:15]1[CH:20]=[CH:19][C:18]([C:2]2[CH:3]=[CH:4][C:5]3[N:6]([C:8](=[O:11])[NH:9][N:10]=3)[CH:7]=2)=[CH:17][CH:16]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 27343864-(Trifluoromethoxy)phenylboronic acidHCID 120407986-bromo-2H,3H-[1,2,4]triazolo[4,3-a]pyridin-3-one

Product 1

HCID 58044589HCID 58044589, compound

Reagents, catalysts & solvents 1

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)Catalyst

Conditions

Temperature
95 °C

Procedure

A mixture of 6.4 g 6-bromo-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one (31.3 mmol), 12.4 g 4-(trifluoromethoxy)phenyl boronic acid (60.0 mmol), 12.4 g potassium carbonate (90.0 mmol), and 1.1 g Pd(dppf)Cl2 in 200 mL degassed 2:1:1 toluene:isopropanol:water was heated at 95° C. in sealed vessel. After 3 days, the aqueous layer was decanted and the organic concentrated. The residue was triturated with ethyl acetate to provide 6-(4-(trifluoromethoxy)phenyl)-[1,2,4]triazolo[4,3-a]pyridin-3(2H)-one as a dark grey solid. m/z (ESI)=226.2 [M+H]+. 1H NMR (δ, d6-DMSO, 400 MHz) 12.55 (s, 1H), 8.07 (s, 1H), 7.82 (d, 2H), 7.56 (dd, 1H), 7.43 (d, 2H), 7.33 (d, 1H)

Workup

  1. customdegassed 2:1:1 toluene
  2. customthe aqueous layer was decanted
  3. customThe residue was triturated with ethyl acetate

Sources & evidence

ORD record
ord-f4746e90face4b4e989b0570f5c235bf
Source dataset
uspto-grants-2014_04
Patent number
US08703759B2

Reaction notes

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