Water → (4-Chloro-benzyl)-(6-fluoro-pyridin-2-yl)-amine

HRID 509945ノート

反応式

HRID 509945 の反応式
F[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=1.[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH2:15])=[CH:12][CH:11]=1.C(N(CC)C(C)C)(C)C.O>CN1CCCC1=O>[Cl:9][C:10]1[CH:17]=[CH:16][C:13]([CH2:14][NH:15][C:2]2[CH:7]=[CH:6][CH:5]=[C:4]([F:8])[N:3]=2)=[CH:12][CH:11]=1

参加物

6

反応物 4

HCID 962WaterHCID 660364-ChlorobenzylamineHCID 739342,6-DifluoropyridineHCID 81531Diisopropylethylamine

生成物 1

HCID 57619459(4-Chloro-benzyl)-(6-fluoro-pyridin-2-yl)-amine収率 67.9%

試薬・触媒・溶媒 1

HCID 13387N-methyl-2-pyrrolidone溶媒

反応条件

温度
90 °C

実験手順

To 2,6-difluoro-pyridine (49, 3.80 g, 33.0 mmol) in 20.0 mL of N-methylpyrrolidone, 4-chloro-benzylamine (50, 5.6 mL, 46.0 mmol) and N,N-diisopropylethylamine (10.0 mL, 57.4 mmol) were added. The reaction was stirred at 90° C. overnight, then poured into water and extracted with ethyl acetate. The organic layer was dried over sodium sulfate, filtered and the filtrate concentrated under vacuum. The resulting material was purified by silica gel column chromatography, eluting with 25% ethyl acetate in hexane. Appropriate fractions were combined and the solvents removed under vacuum, and the resulting material was washed with ethyl acetate/hexane to provide the desired compound as a white solid (51, 5.30 g).

後処理

  1. extractionextracted with ethyl acetate
  2. dry with materialThe organic layer was dried over sodium sulfate
  3. filtrationfiltered
  4. concentrationthe filtrate concentrated under vacuum
  5. customThe resulting material was purified by silica gel column chromatography
  6. washeluting with 25% ethyl acetate in hexane
  7. customthe solvents removed under vacuum
  8. washthe resulting material was washed with ethyl acetate/hexane

出典と根拠

ORDレコード
ord-78fe8996176e45529eb993dfc9b23bb8
出典データセット
uspto-grants-2015_08
特許番号
US09096593B2

反応ノート

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