(4-Methoxyphenyl)boronic acid → 5-Bromo-N-(4-methoxyphenyl)pyrazin-2-amine

HRID 1642272

반응식

HRID 1642272 반응식
[CH3:1][O:2][C:3]1[CH:8]=[CH:7][C:6](B(O)O)=[CH:5][CH:4]=1.[Br:12][C:13]1[N:14]=[CH:15][C:16]([NH2:19])=[N:17][CH:18]=1>CN(C1C=CN=CC=1)C.C(Cl)Cl.CC([O-])=O.CC([O-])=O.[Cu+2]>[Br:12][C:13]1[N:14]=[CH:15][C:16]([NH:19][C:6]2[CH:7]=[CH:8][C:3]([O:2][CH3:1])=[CH:4][CH:5]=2)=[N:17][CH:18]=1

참가 물질

6

반응물 2

HCID 201262(4-Methoxyphenyl)boronic acidHCID 5995392-Amino-5-bromopyrazine

생성물 1

HCID 534150715-Bromo-N-(4-methoxyphenyl)pyrazin-2-amine수율 10.4%

시약·촉매·용매 3

HCID 8895Cupric acetate촉매HCID 142844-(Dimethylamino)pyridine촉매HCID 6344Dichloromethane용매

실험 절차

Into a 50 mL roundbottom flask, was placed 4-methoxyphenylboronic acid (5.4 g, 35.54 mmol). To this was added 5-bromo-pyrazin-2-ylamine (3 g, 17.24 mmol). Cu(OAc)2 (3.45 g, 19.06 mmol) was added, followed by addition of a solution of DMAP (4.2 g, 34.43 mmol) in CH2Cl2 (20 mL). The resulting solution was stirred at room temperature for 12 hours. The reaction progress was monitored by thin layer chromatography (TLC) (ethyl acetate/petroleum ether=1:2). When the reaction was complete, the mixture was filtered, then concentrated under vacuum. The residue was dissolved in ethyl acetate (EtOAc), then washed with water. The organic layer was dried over Na2SO4, then filtered and concentrated. The crude product was purified by silica gel chromatography (SGC) eluting with ethyl acetate/petroleum ether (1:5, v/v) to provide (5-bromo-pyrazin-2-yl)-(4-methoxy-phenyl)-amine (i) (500 mg, yield 10%) as a yellow solid.

후처리

  1. customInto a 50 mL roundbottom flask, was placed
  2. filtrationthe mixture was filtered
  3. concentrationconcentrated under vacuum
  4. dissolutionThe residue was dissolved in ethyl acetate (EtOAc)
  5. washwashed with water
  6. dry with materialThe organic layer was dried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe crude product was purified by silica gel chromatography (SGC)
  10. washeluting with ethyl acetate/petroleum ether (1:5

출처 및 근거

ORD 기록
ord-425ee4b87c6f4d188a081842f9a4f50e
출처 데이터셋
uspto-grants-2012_02
특허 번호
US08119643B2

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