Cyclohexene → HCID 15859429, compound

HRID 1378677Notes

Reaction equation

HRID 1378677 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[N:11]=[C:12]2[C:22]3[CH2:21][CH2:20][CH2:19][CH2:18][C:17]=3[NH:16][C:13]2=[N:14][CH:15]=1.C1CCCCC=1>[Pd].C1(C)C=C(C)C=C(C)C=1>[F:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][CH3:9])=[CH:4][C:3]=1[C:10]1[N:11]=[C:12]2[C:22]3[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=3[NH:16][C:13]2=[N:14][CH:15]=1

Participants

5

Reactant 2

HCID 8079CyclohexeneHCID 9926219HCID 9926219, compound

Product 1

HCID 15859429HCID 15859429, compound

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 7947MesityleneSolvent

Conditions

Temperature
200 °C

Procedure

A sealed tube containing 2-(2-Fluoro-5-methoxyphenyl)-6,7,8,9-tetrahydro-indolo[2,3-b]pyrazine (46 mg, 0.155 mmol), cyclohexene (10 equiv., 0.157 mL, 1.55 mmol), Pd black (35 mg) and mesitylene (10 mL) was heated to 200° C. in an oil bath and the contents stirred via a magnetic stir bar. The progress of the reaction was monitored by intermittently opening the cooled tube and taking out an aliquot for TLC analysis (30% ethyl acetate/hexanes eluent; the aromatized product has a slightly larger Rf value than that of the starting material). Upon completion of the reaction, the mixture was filtered through celite and the mesitylene removed using a high vacuum rotary evaporator. Recrystallization from hexanes/ethyl acetate afforded 2-(2-Fluoro-5-methoxyphenyl)-5H-indolo[2,3-b]pyrazine (Compound 2) as an off-white solid.

Workup

  1. customUpon completion of the reaction
  2. filtrationthe mixture was filtered through celite
  3. customthe mesitylene removed
  4. customa high vacuum rotary evaporator
  5. customRecrystallization from hexanes/ethyl acetate

Sources & evidence

ORD record
ord-3307ec73c4ad4322a65497d7b09a898d
Source dataset
uspto-grants-1997_09
Patent number
US05668283

Reaction notes

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