Methyl iodide → 5-Bromo-N-methylpyridin-2-amine

HRID 225873ノート

反応式

HRID 225873 の反応式
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[CH:8][C:7]([Br:10])=[CH:6][N:5]=1.[CH3:11]I>CN(C=O)C>[Br:10][C:7]1[CH:8]=[CH:9][C:4]([NH:3][CH3:11])=[N:5][CH:6]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 706222-Amino-5-bromopyridine

生成物 1

HCID 156456635-Bromo-N-methylpyridin-2-amine収率 32.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

To a suspension of NaH (60% dispersion in mineral oil, 0.44 g, 11 mmole) in dry DMF (40 mL) was added solid 2-amino-5-bromopyridine (1.73 g, 10 mmole) in portions over 5-10 min. Gas evolution was allowed to subside between additions. The resulting amber mixture was stirred for 15 min, then methyl iodide (0.61 mL, 10 mmole) was added all at once. The reaction mixture was stirred at RT overnight, then was concentrated in vacuo. The residue was diluted with 5% NH4Cl (30 mL) and the mixture was extracted with CH2Cl2. The combined organic extracts were washed with brine, dried (MgSO4), and concentrated. Flash chromatography on silica gel (3% MeOH/CH2Cl2) separated the products. 5-Bromo-2-(methylamino)pyridine (0.60 g, 32%) was obtained as a semisolid: TLC (3% MeOH(CH2Cl2) Rf 0.35; MS (ES) m/e 187 (M+H)+. 5-Bromo-2-(dimethylamino)pyridine (0.70 g, 34%) was obtained as a semisolid: TLC (3% MeOH/CH2Cl2) Rf 0.77; MS (ES) m/e 201 (M+H)+.

後処理

  1. stirringThe reaction mixture was stirred at RT overnight
  2. concentrationwas concentrated in vacuo
  3. additionThe residue was diluted with 5% NH4Cl (30 mL)
  4. extractionthe mixture was extracted with CH2Cl2
  5. washThe combined organic extracts were washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated
  8. customFlash chromatography on silica gel (3% MeOH/CH2Cl2) separated the products

出典と根拠

ORDレコード
ord-9203da0898b4452faf19ae5b7ab00fbf
出典データセット
uspto-grants-2009_07
特許番号
US07557125B2

反応ノート

読み込み中…