Toluene → HCID 20567052, compound

HRID 1524049Notes

Reaction equation

HRID 1524049 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5](B(O)O)=[CH:4][CH:3]=1.Br[C:12]1[N:13]=[CH:14][C:15]([NH2:18])=[N:16][CH:17]=1.C1(C)C=CC=CC=1.C([O-])([O-])=O.[K+].[K+]>C(OCC)(=O)C.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.C(O)C>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:12]2[N:13]=[CH:14][C:15]([NH2:18])=[N:16][CH:17]=2)=[CH:4][CH:3]=1

Participants

9

Reactant 4

HCID 1140TolueneHCID 11430Potassium CarbonateHCID 79599(4-Bromophenyl)boronic acidHCID 5995392-Amino-5-bromopyrazine

Product 1

HCID 20567052HCID 20567052, compound

Reagents, catalysts & solvents 4

HCID 178418397HCID 178418397, compoundCatalystHCID 702EthanolSolventHCID 962WaterSolventHCID 8857Ethyl AcetateSolvent

Conditions

Temperature
50 °C

Procedure

(4-Bromophenyl)boronic acid (100 mg, 0.498 mmol) and 5-bromopyrazin-2-amine (173 mg, 0.996 mmol) were added to a 5 mL sealable vial equipped with a stir bar. To this vial was added toluene (1.5 mL), ethanol (1.5 mL) and K2CO3(0.7 mL, 2 M). The solvent was sparged with argon for 10 min before adding Pd(PPh3)4 (17 mg, 0.004 mmol), the vial sealed and the mixture stirred at 50° Celsius for 15 hours. The reaction was cooled to rt and then diluted with ethyl acetate (50 mL) and water (50 mL) and the layers separated. The aqueous layer was further extracted with ethyl acetate (3×50 mL). The combined organic extracts were dried with Na2SO4 and concentrated to dryness. The crude material was purified FCC to give 5-(4-bromophenyl)pyrazin-2-amine. 1H NMR (500 MHz, CDCl3) δ 8.52-8.31 (d, J=1.5, 1H), 8.08-7.95 (d, J=1.6, 1H), 7.86-7.71 (d, J=8.4, 2H), 7.63-7.49 (d, J=8.6, 2H), 4.70 (s, 2H).

Workup

  1. customequipped with a stir bar
  2. customThe solvent was sparged with argon for 10 min
  3. customthe vial sealed
  4. temperatureThe reaction was cooled to rt
  5. customthe layers separated
  6. extractionThe aqueous layer was further extracted with ethyl acetate (3×50 mL)
  7. dry with materialThe combined organic extracts were dried with Na2SO4
  8. concentrationconcentrated to dryness
  9. customThe crude material was purified FCC

Sources & evidence

ORD record
ord-94e585204d674ae5aa346b2acf76d9ab
Source dataset
uspto-grants-2015_07
Patent number
US09079866B2

Reaction notes

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