Benzyl Bromide → 5-(Dibenzylamino)picolinonitrile

HRID 55881

反応式

HRID 55881 の反応式
[NH2:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[H-].[Na+].[CH2:12](Br)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1>CN(C=O)C.O>[CH2:12]([N:1]([CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[C:2]1[CH:3]=[CH:4][C:5]([C:8]#[N:9])=[N:6][CH:7]=1)[C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1

参加物

6

反応物 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 38713955-Aminopyridine-2-carbonitrile

生成物 1

HCID 666069135-(Dibenzylamino)picolinonitrile収率 65%

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 6228Dimethylformamide溶媒

実験手順

To a solution of 5-amino-pyridine-2-carbonitrile (37) (800 mg, 6.72 mmol) in DMF (8 mL) was added NaH (60%) (806 mg, 20.2 mmol) portion wise at 0° C. Benzyl bromide (2.3 mL, 20.2 mmol) was subsequently added and the mixture allowed to stir at rt for 3 h. The reaction mixture was diluted with water (20 mL), extracted with EtOAc (2×50 mL), the combined organic layers were washed with brine (20 mL), dried (Na2SO4) and evaporated. The crude compound was purified by silica gel column chromatography (100-200 mesh, eluted with 30% EtOAc/pet-ether) to obtain compound 38 (1.3 g, 65%) as a pale yellow solid. Rf: 0.7 (10% MeOH/CHCl3); (m/z): 300 [MH]+; 1H NMR (400 MHz, DMSO-d6): δ 8.14 (1H, d, J=2.8 Hz), 7.65 (1H, d, J=9.2 Hz), 7.37-7.25 (10H, m), 7.08 (1H, dd, J=3.6, 9.6 Hz), δ 4.88 (4H, s).

後処理

  1. extractionextracted with EtOAc (2×50 mL)
  2. washthe combined organic layers were washed with brine (20 mL)
  3. dry with materialdried (Na2SO4)
  4. customevaporated
  5. customThe crude compound was purified by silica gel column chromatography (100-200 mesh, eluted with 30% EtOAc/pet-ether)

出典と根拠

ORDレコード
ord-061c8828ff45484eb01195d598bfbd49
出典データセット
uspto-grants-2016_09
特許番号
US09433622B2

関連ノート

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