Sodium Carbonate → HCID 15953666, compound

HRID 271404Notes

Reaction equation

HRID 271404 reaction equation
Br[C:2]1[C:3]2[N:4]([C:9](=[O:23])[N:10]([CH2:12][C:13]3[CH:14]=[N:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=3)[N:11]=2)[CH:5]=[N:6][C:7]=1Cl.[Cl:24][C:25]1[CH:30]=[CH:29][C:28](B(O)O)=[CH:27][CH:26]=1.C([O-])([O-])=O.[Na+].[Na+]>C1(C)C=CC=CC=1.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:24][C:25]1[CH:30]=[CH:29][C:28]([C:7]2[N:6]=[CH:5][N:4]3[C:9](=[O:23])[N:10]([CH2:12][C:13]4[CH:14]=[N:15][C:16]([C:19]([F:22])([F:21])[F:20])=[CH:17][CH:18]=4)[N:11]=[C:3]3[C:2]=2[C:28]2[CH:29]=[CH:30][C:25]([Cl:24])=[CH:26][CH:27]=2)=[CH:27][CH:26]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 742994-Chlorophenylboronic acidHCID 58772841HCID 58772841, compound

Product 1

HCID 15953666HCID 15953666, compoundYield 9.8%

Reagents, catalysts & solvents 2

HCID 178418397HCID 178418397, compoundCatalystHCID 1140TolueneSolvent

Conditions

Temperature
100 °C

Procedure

To a solution of 8-bromo-7-chloro-2-((6-(trifluoromethyl)pyridin-3-yl)methyl)-[1,2,4]triazolo[4,3-c]pyrimidin-3(2H)-one (81.3 mg, 0.20 mmol) in toluene (3 mL) at room temperature under argon was added 4-chlorophenylboronic acid (46.8 mg, 0.30 mmol), tetrakis(triphenylphosphine)palladium (46 mg, 0.040 mmol), and aqueous Na2CO3 solution (2.0 M, 0.20 mL, 0.40 mmol). The resulting suspension was stirred and heated at 100° C. under argon for 22 h. Analysis by HPLC/MS indicated that starting material had been consumed. After the reaction mixture was cooled to room temperature, water (10 mL) and EtOAc (15 mL) were added. The layers were separated. The organic layer was dried (Na2SO4), filtered, and concentrated under reduced pressure. The crude product was purified by silica gel column chromatography eluted with ethyl acetate-hexanes to obtain the title compound (7.6 mg) as an off-white solid. HPLC/MS: retention time=4.10 min, [M+H]30 =516.

Workup

  1. customhad been consumed
  2. temperatureAfter the reaction mixture was cooled to room temperature
  3. additionwater (10 mL) and EtOAc (15 mL) were added
  4. customThe layers were separated
  5. dry with materialThe organic layer was dried (Na2SO4)
  6. filtrationfiltered
  7. concentrationconcentrated under reduced pressure
  8. customThe crude product was purified by silica gel column chromatography
  9. washeluted with ethyl acetate-hexanes

Sources & evidence

ORD record
ord-f05b9a756a0249eb9805db3c3f445885
Source dataset
uspto-grants-2008_11
Patent number
US07452892B2

Reaction notes

Loading…