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

HRID 78690ノート

反応式

HRID 78690 の反応式
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]

参加物

6

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 24290Palladium Chloride触媒HCID 10311-Propanol溶媒

実験手順

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]+.

後処理

  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

出典と根拠

ORDレコード
ord-ab15c8356f42442d9e4fa941495595d6
出典データセット
uspto-grants-2014_09
特許番号
US08841450B2

反応ノート

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