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

HRID 225873노트

반응식

HRID 225873 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

HCID 156456635-Bromo-N-methylpyridin-2-amine수율 32.1%

시약·촉매·용매 1

HCID 6228Dimethylformamide용매

실험 절차

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)+.

후처리

  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

출처 및 근거

ORD 기록
ord-9203da0898b4452faf19ae5b7ab00fbf
출처 데이터셋
uspto-grants-2009_07
특허 번호
US07557125B2

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