Potassium vinyltrifluoroborate → 5-(4-(Isopropylsulfonyl)phenyl)-3-vinylpyrazin-2-amine

HRID 78690Notes

Reaction equation

HRID 78690 reaction equation
Br[C:2]1[C:3]([NH2:20])=[N:4][CH:5]=[C:6]([C:8]2[CH:13]=[CH:12][C:11]([S:14]([CH:17]([CH3:19])[CH3:18])(=[O:16])=[O:15])=[CH:10][CH:9]=2)[N:7]=1.F[B-](F)(F)[CH:23]=[CH2:24].[K+]>C(O)CC.Cl[Pd]Cl.[Fe]>[CH:17]([S:14]([C:11]1[CH:12]=[CH:13][C:8]([C:6]2[N:7]=[C:2]([CH:23]=[CH2:24])[C:3]([NH2:20])=[N:4][CH:5]=2)=[CH:9][CH:10]=1)(=[O:16])=[O:15])([CH3:19])[CH3:18]

Participants

6

Reactant 2

HCID 23679353Potassium vinyltrifluoroborateHCID 580843723-Bromo-5-(4-(isopropylsulfonyl)phenyl)pyrazin-2-amine

Product 1

HCID 866827695-(4-(Isopropylsulfonyl)phenyl)-3-vinylpyrazin-2-amine

Reagents, catalysts & solvents 3

HCID 23925IronCatalystHCID 24290Palladium ChlorideCatalystHCID 10311-PropanolSolvent

Procedure

dichloropalladium; iron (155.6 mg, 0.2132 mmol) was added to a solution of 3-bromo-5-(4-isopropylsulfonylphenyl)pyrazin-2-amine (455.6 mg, 1.279 mmol), TEA (323.6 mg, 445.7 μL, 3.198 mmol) and potassium trifluoro(vinyl)boranuide (171.3 mg, 1.279 mmol) in propanol (2 mL). The reaction mixture was heated in a microwave for 40 min at 100 C. The reaction mixture was concentrated in vacuo. The residue was partitioned between DCM and water. The organic extract was dried over MgSO4 and concentrated in vacuo yielding an oil that was purified by chromatography on silica using 100% DCM to DCM/MeOH 90/10 as elaunt to yield 5-(4-(isopropylsulfonyl)phenyl)-3-vinylpyrazin-2-amine as an orange solid. LC/MS m/z 304.3 [M+1]+.

Workup

  1. temperatureThe reaction mixture was heated in a microwave for 40 min at 100 C
  2. concentrationThe reaction mixture was concentrated in vacuo
  3. customThe residue was partitioned between DCM and water
  4. extractionThe organic extract
  5. dry with materialwas dried over MgSO4
  6. concentrationconcentrated in vacuo
  7. customyielding an oil that
  8. customwas purified by chromatography on silica using 100% DCM to DCM/MeOH 90/10 as elaunt

Sources & evidence

ORD record
ord-ab15c8356f42442d9e4fa941495595d6
Source dataset
uspto-grants-2014_09
Patent number
US08841450B2

Reaction notes

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