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

HRID 1030097

反応式

HRID 1030097 の反応式
[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]

参加物

6

反応物 4

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-5 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-d52e31073cdd4be18443743cf47c3f6f
出典データセット
uspto-grants-1992_04
特許番号
US05104876

関連ノート

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