Ammonium Chloride → 3-(4-Bromo-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one

HRID 1617505ノート

反応式

HRID 1617505 の反応式
[Li]CCCC.Br[C:7]1[CH:12]=[CH:11][N:10]=[C:9]([CH3:13])[CH:8]=1.[Br:14][C:15]1[CH:20]=[CH:19][C:18]([CH:21]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])[CH2:22][C:23](N(OC)C)=[O:24])=[CH:17][CH:16]=1.[NH4+].[Cl-]>C1COCC1>[Br:14][C:15]1[CH:16]=[CH:17][C:18]([CH:21]([C:29]2[CH:34]=[CH:33][CH:32]=[CH:31][C:30]=2[CH3:35])[CH2:22][C:23]([C:7]2[CH:12]=[CH:11][N:10]=[C:9]([CH3:13])[CH:8]=2)=[O:24])=[CH:19][CH:20]=1

参加物

6

反応物 4

HCID 25517Ammonium ChlorideHCID 27628354-Bromo-2-methylpyridineHCID 866609493-(4-Bromo-phenyl)-N-methoxy-N-methyl-3-o-tolyl-propionamideHCID 178418339Butyllithium

生成物 1

HCID 666681803-(4-Bromo-phenyl)-1-(2-methyl-pyridin-4-yl)-3-o-tolyl-propan-1-one収率 55%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒2 回

反応条件

温度
-70 °C

実験手順

To a solution of n-BuLi (12.9 mL 1.6 M in hexane) was added dropwise a solution of 4-bromo-2-methylpyridine (3.56 g) in THF (170 mL) at −70° C. over a period of 20 min. The reaction mixture was stirred at −70° C. for 5 min, before a solution of 3-(4-bromo-phenyl)-N-methoxy-N-methyl-3-o-tolyl-propionamide (2.5 g) in THF (100 mL) was added dropwise. After the addition was complete, the mixture was stirred at −70° C. for 3 hours. A saturated solution of NH4Cl was added, the phases were separated and the inorganic one was extracted with EtOAc (2×). The combined organic layers were washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 1:1) to give the title compound as an yellow oil (1.49 g, 55%), MS (ESI+): m/z=394.0797 ([M+H]+, 1Br).

後処理

  1. additionwas added dropwise
  2. additionAfter the addition
  3. customthe phases were separated
  4. extractionthe inorganic one was extracted with EtOAc (2×)
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated in vacuo
  9. customThe crude product was purified by flash chromatography on silica gel (EtOAc/n-heptane 1:1)

出典と根拠

ORDレコード
ord-a3dccd2b4ee94ae2be82da43bba1a661
出典データセット
uspto-grants-2014_07
特許番号
US08765730B2

反応ノート

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