Potassium Phosphate, Tribasic → 5-(4-(Isopropylsulfonyl)phenyl)pyrazin-2-amine

HRID 68652

반응식

HRID 68652 반응식
Br[C:2]1[N:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=1.[CH:9]([S:12]([C:15]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17][CH:16]=1)(=[O:14])=[O:13])([CH3:11])[CH3:10].[O-]P([O-])([O-])=O.[K+].[K+].[K+]>CC#N.CCOC(C)=O.O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[CH:9]([S:12]([C:15]1[CH:20]=[CH:19][C:18]([C:2]2[N:3]=[CH:4][C:5]([NH2:8])=[N:6][CH:7]=2)=[CH:17][CH:16]=1)(=[O:13])=[O:14])([CH3:11])[CH3:10]

참가 물질

8

반응물 3

HCID 62657Potassium Phosphate, TribasicHCID 5995392-Amino-5-bromopyrazineHCID 441193274-(Isopropylsulphonyl)benzeneboronic acid

생성물 1

HCID 580843825-(4-(Isopropylsulfonyl)phenyl)pyrazin-2-amine수율 80.7%

시약·촉매·용매 4

HCID 178418851HCID 178418851, 화합물촉매HCID 962Water용매2회HCID 6342Acetonitrile용매HCID 8857Ethyl Acetate용매

반응 조건

온도
60 °C

실험 절차

5-Bromopyrazin-2-amine (5 g, 28.74 mmol), (4-isopropylsulfonylphenyl) boronic acid (7.866 g, 34.49 mmol) and K3PO4 (12.20 g, 57.48 mmol) were combined in MeCN (100 mL)/Water (25 mL) and Pd[P(tBu)3]2 (734.4 mg, 1.437 mmol) was added. The reaction was heated at 60° C. for 1 hour. The reaction mixture was cooled to ambient temperature and diluted with EtOAc and water. The layers were separated and the aqueous layer extracted with EtOAc (×3). The combined organic layers were dried (MgSO4), filtered and concentrated in vacuo. The residue was triturated from DCM and isolated by filtration to give the sub-title compound as an orange solid (6.43 g, 76% Yield). 1H NMR (400.0 MHz, DMSO) δ 1.17 (d, 6H), 3.43 (sept, 1H), 6.86 (s, 2H), 7.87 (d, 2H), 8.00 (s, 1H), 8.20 (d, 2H) and 8.67 (s, 1H) ppm; MS (ES+) 278.2.

후처리

  1. additionwas added
  2. temperatureThe reaction mixture was cooled to ambient temperature
  3. customThe layers were separated
  4. extractionthe aqueous layer extracted with EtOAc (×3)
  5. dry with materialThe combined organic layers were dried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was triturated from DCM
  9. customisolated by filtration

출처 및 근거

ORD 기록
ord-61a69da484c1490a8b1889e647c37046
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08822469B2

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