HCID 69083514, compound → HCID 69082945, compound

HRID 1852896Notes

Reaction equation

HRID 1852896 reaction equation
[CH3:1][C:2]([C:7]1[C:12]([C:13]#[C:14][C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([F:24])([F:23])[F:22])=[N:11][CH:10]=[CH:9][N:8]=1)([CH3:6])[C:3]([OH:5])=[O:4]>C(Cl)(Cl)(Cl)Cl.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Au](Cl)(Cl)Cl.F[B-](F)(F)F.[Ag+]>[CH3:6][C:2]1([CH3:1])[C:7]2[C:12](=[N:11][CH:10]=[CH:9][N:8]=2)/[C:13](=[CH:14]/[C:15]2[CH:20]=[CH:19][CH:18]=[CH:17][C:16]=2[C:21]([F:23])([F:24])[F:22])/[O:4][C:3]1=[O:5]

Participants

5

Reactant 1

HCID 69083514HCID 69083514, compound

Product 1

HCID 69082945HCID 69082945, compoundYield 34%

Reagents, catalysts & solvents 3

HCID 159722Silver tetrafluoroborateCatalystHCID 11169040HCID 11169040, compoundCatalystHCID 5943Carbon TetrachlorideSolvent

Conditions

Temperature
55 °C

Procedure

A solution of gold chloride triphenylphosphine (0.444 g) and silver tetrafluoroborate (0.174 g) in carbon tetrachloride was stirred for 30 min. To this solution was added a solution of 2-methyl-2-[3-(2-trifluoromethyl-phenylethynyl)-pyrazin-2-yl]-propionic acid (0.50 g). The reaction mixture was flushed out with argon then heated to 55° C. for 48 hours. The reaction mixture was cooled to ambient temperature, filtered, concentrated and the residue purified by chromatography on silica gel (eluent 5-95% ethyl acetate in isohexane) to give 8,8-dimethyl-5-[1-(2-trifluoromethyl-phenyl)-meth-(Z)-ylidene]-5,8-dihydro-pyrano[3,4-b]pyrazin-7-one (compound D1 of Table D) (0.170 g).

Workup

  1. customThe reaction mixture was flushed out with argon
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. filtrationfiltered
  4. concentrationconcentrated
  5. customthe residue purified by chromatography on silica gel (eluent 5-95% ethyl acetate in isohexane)

Sources & evidence

ORD record
ord-f67acf28e99f48ac935ecd4c31648f58
Source dataset
uspto-grants-2015_02
Patent number
US08962628B2

Reaction notes

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