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

HRID 78690노트

반응식

HRID 78690 반응식
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]

참가 물질

6

반응물 2

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

생성물 1

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

시약·촉매·용매 3

HCID 23925Iron촉매HCID 24290Palladium Chloride촉매HCID 10311-Propanol용매

실험 절차

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]+.

후처리

  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

출처 및 근거

ORD 기록
ord-ab15c8356f42442d9e4fa941495595d6
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08841450B2

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