Sodium hydride → N-[(2-chloropyridin-3-yl)methyl]-N-pyridin-3-ylpyridin-3-amine

HRID 563947

反応式

HRID 563947 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[C:3]([NH:7][C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[CH:2]=1.[H-].[Na+].Br[CH2:17][C:18]1[C:19]([Cl:24])=[N:20][CH:21]=[CH:22][CH:23]=1>CN(C=O)C.C(OCC)(=O)C>[Cl:24][C:19]1[C:18]([CH2:17][N:7]([C:8]2[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=2)[C:3]2[CH:2]=[N:1][CH:6]=[CH:5][CH:4]=2)=[CH:23][CH:22]=[CH:21][N:20]=1

参加物

6

反応物 3

HCID 24758Sodium hydrideHCID 598775N-pyridin-3-ylpyridin-3-amineHCID 189310283-(Bromomethyl)-2-chloropyridine

生成物 1

HCID 59138879N-[(2-chloropyridin-3-yl)methyl]-N-pyridin-3-ylpyridin-3-amine収率 77%

試薬・触媒・溶媒 2

HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

To a solution of N-pyridin-3-ylpyridin-3-amine (510 mg, 3 mmol) in anhydrous DMF (4.5 mL) was added 60% sodium hydride/mineral oil (169 mg, 4.2 mmol). After stirring at ambient temperature for 15 min., 3-(bromomethyl)-2-chloropyridine (677 mg, 3.28 mmol) (preparation described in U.S. Pat. No. 5,739,326) was added neat and the action was stirred for ˜2 hours. The reaction was diluted with ethyl acetate, washed with NaHCO3 solution, then water, and the organic layer was dried over anhydrous sodium sulfate, filtered, and the solvent evaporated. The residue was purified by silica gel chromato-graphy eluting with a 20-90% acetonelhexane gradient to give the purified product which upon trituration with diethyl ether gave the title compound as a tan solid (684 mg, 77% yield). 1H-NMR (500 MHz , CDCl3): δ 8.40 (2H, d, J=2.7 Hz), 8.34 (1H, d, J=4.6 Hz), 8.30 (2H, d, J=4.6 Hz), 7.69 (1H, d, J=7.8 Hz), 7.33-7.35 (2H, br d, J=˜8.3 Hz), 7.20-7.26 (4H, m), 5.04 (2H, s). m/e (m+1): 297.0

後処理

  1. addition5,739,326) was added neat
  2. stirringthe action was stirred for ˜2 hours
  3. washwashed with NaHCO3 solution
  4. dry with materialwater, and the organic layer was dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. customthe solvent evaporated
  7. customThe residue was purified by silica gel chromato-graphy
  8. washeluting with a 20-90% acetonelhexane gradient
  9. customto give the purified product which upon trituration with diethyl ether

出典と根拠

ORDレコード
ord-c65ed67f66f942c183feac62d2d24622
出典データセット
uspto-grants-2011_11
特許番号
US08067607B2

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