1-(2-Chloroethyl)-4-fluorobenzene → N-(1,1-Dimethylethyl)-3-[3-(4-fluorophenyl)propyl]-5-methyl-2-pyridine carboxamide

HRID 1030097

반응식

HRID 1030097 반응식
[CH3:1][C:2]([NH:5][C:6]([C:8]1[C:13]([CH3:14])=[CH:12][CH:11]=[CH:10][N:9]=1)=[O:7])([CH3:4])[CH3:3].[CH2:15]([Li])CCC.[Br-].[Na+].[F:22][C:23]1[CH:31]=[CH:30][C:26]([CH2:27][CH2:28]Cl)=[CH:25][CH:24]=1>C1COCC1>[CH3:4][C:2]([NH:5][C:6]([C:8]1[C:13]([CH2:14][CH2:28][CH2:27][C:26]2[CH:30]=[CH:31][C:23]([F:22])=[CH:24][CH:25]=2)=[CH:12][C:11]([CH3:15])=[CH:10][N:9]=1)=[O:7])([CH3:1])[CH3:3]

참가 물질

6

반응물 4

HCID 676221-(2-Chloroethyl)-4-fluorobenzeneHCID 253881Sodium BromideHCID 5463796N-tert-Butyl-3-methylpyridine-2-carboxamideHCID 178418339Butyllithium

생성물 1

HCID 19821696N-(1,1-Dimethylethyl)-3-[3-(4-fluorophenyl)propyl]-5-methyl-2-pyridine carboxamide

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
-5 °C

실험 절차

Cool a solution of N-(1,1-dimethylethyl)-3-methyl-2-pyridinecarboxamide in dry THF to -40° C. and add 2 equivalents of n-butyl lithium. Add a large excess of sodium bromide and stir for 15 minutes. Add 1 eq. of 4-fluorophenethyl chloride and stir for 2.5 hours while warming to -5° C. Quench the reaction with water and extract the product twice with ethyl acetate, then wash with brine (2X). Dry the organic phase over Na2SO4, filter and remove the solvent to produce the title compound.

후처리

  1. stirringstir for 2.5 hours
  2. customQuench
  3. customthe reaction with water
  4. extractionextract the product twice with ethyl acetate
  5. washwash with brine (2X)
  6. dry with materialDry the organic phase over Na2SO4
  7. filtrationfilter
  8. customremove the solvent

출처 및 근거

ORD 기록
ord-d52e31073cdd4be18443743cf47c3f6f
출처 데이터셋
uspto-grants-1992_04
특허 번호
US05104876

연결된 노트

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