Pyridine → 2-Amino-3-bromo-5-(4-methoxyphenyl)pyrazine

HRID 1034592ノート

反応式

HRID 1034592 の反応式
[NH2:1][C:2]1[CH:7]=[N:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:4][N:3]=1.N1C=CC=CC=1.[Br:22]Br>C(Cl)(Cl)Cl>[NH2:1][C:2]1[C:7]([Br:22])=[N:6][C:5]([C:8]2[CH:13]=[CH:12][C:11]([O:14][CH3:15])=[CH:10][CH:9]=2)=[CH:4][N:3]=1

参加物

5

反応物 3

HCID 1049PyridineHCID 24408BromineHCID 156743865-(4-Methoxyphenyl)pyrazin-2-amine

生成物 1

HCID 715237102-Amino-3-bromo-5-(4-methoxyphenyl)pyrazine収率 70%

試薬・触媒・溶媒 1

HCID 6212Chloroform溶媒2 回

実験手順

To a solution of 2-amino-5-(4-mcthoxyphenyl)pyrazinc 16a (0.35 g, 1.7 mmol) and pyridine (0.20 mL, 2.6 mmol) in chloroform (20 mL), bromine (Br2) (0.13 mL, 2.6 mmol) was added dropwise in chloroform (3 mL) at −10° C. After 6 h stirring at room temperature, the reaction mixture was washed with water, the organic layer dried over Na2SO4, filtered and the solvent was removed under reduced pressure. The crude product was purified by flash chromatography using dichloromethane-EtOAc (90:10 v/v) as eluent, to obtain 0.33 g of 17a as an brown solid (mp 166-170° C., 70% yield). 1H-NMR (CDCl3): 3.83 (s, 3H), 5.04 (br s, 2H), 6.92-6.96 (m, 2H), 7.76-7.80 (m, 2H), 8.31 (s, 1H). GC-MS (EI): m/z 279,281 (M1, 100).

後処理

  1. washthe reaction mixture was washed with water
  2. dry with materialthe organic layer dried over Na2SO4
  3. filtrationfiltered
  4. customthe solvent was removed under reduced pressure
  5. customThe crude product was purified by flash chromatography

出典と根拠

ORDレコード
ord-fa0d033ad63b4d21ba822ff8ba9e0442
出典データセット
uspto-grants-2013_10
特許番号
US08546147B2

反応ノート

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