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

HRID 509945노트

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HRID 509945 반응식
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

참가 물질

6

반응물 4

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

생성물 1

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

시약·촉매·용매 1

HCID 13387N-methyl-2-pyrrolidone용매

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온도
90 °C

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-78fe8996176e45529eb993dfc9b23bb8
출처 데이터셋
uspto-grants-2015_08
특허 번호
US09096593B2

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