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

HRID 1915028

反応式

HRID 1915028 の反応式
[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>[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6344Dichloromethane溶媒

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-0020134caac8437ebf63ccc4b209b20c
出典データセット
uspto-grants-2013_12
特許番号
US08614321B2

関連ノート

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