Ethanesulfonamide → N-((5-(3-chloro-4-cyanophenyl)pyridin-3-yl)(cyclopropyl)methyl)ethanesulfonamide

HRID 1897772ノート

反応式

HRID 1897772 の反応式
[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:11]=[N:12][CH:13]=[C:14]([CH:16]=O)[CH:15]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[CH2:18]([S:20]([NH2:23])(=[O:22])=[O:21])[CH3:19].[CH:24]1([Mg]Br)[CH2:26][CH2:25]1>C1(C)C=CC=CC=1.CC(C)[O-].[Ti+4].CC(C)[O-].CC(C)[O-].CC(C)[O-]>[Cl:1][C:2]1[CH:9]=[C:8]([C:10]2[CH:15]=[C:14]([CH:16]([CH:24]3[CH2:26][CH2:25]3)[NH:23][S:20]([CH2:18][CH3:19])(=[O:22])=[O:21])[CH:13]=[N:12][CH:11]=2)[CH:7]=[CH:6][C:3]=1[C:4]#[N:5]

参加物

6

反応物 3

HCID 73702EthanesulfonamideHCID 595783972-Chloro-4-(5-formyl-pyridin-3-yl)-benzonitrileHCID 178418630HCID 178418630、化合物

生成物 1

HCID 49819978N-((5-(3-chloro-4-cyanophenyl)pyridin-3-yl)(cyclopropyl)methyl)ethanesulfonamide

試薬・触媒・溶媒 2

HCID 11026Titanium isopropoxide触媒HCID 1140Toluene溶媒

反応条件

温度
-40 °C

実験手順

Titanium(IV) isopropoxide (0.365 mL, 1.245 mmol) was added to a mixture of 2-chloro-4-(5-formylpyridin-3-yl)benzonitrile (as prepared in Example 23, step 1; 0.151 g, 0.622 mmol), ethanesulfonamide (0.085 g, 0.778 mmol) in toluene (10 mL) at room temperature. The resulting mixture was heated to reflux for 4 h. After concentration, the residue was dissolved in THF (5 mL), and cooled to −40° C. Cyclopropylmagnesium bromide (3.73 mL, 1.867 mmol) was added dropwise, and the resulting mixture was slowly warmed up to room temperature and stirred overnight. After quenching by saturated NH4Cl solution, the residue was purified by flash column (ethyl acetate-heptane, v/v, 40%-60%) yielded a slightly yellow solid.

後処理

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux for 4 h
  3. concentrationAfter concentration
  4. dissolutionthe residue was dissolved in THF (5 mL)
  5. temperaturethe resulting mixture was slowly warmed up to room temperature
  6. customAfter quenching by saturated NH4Cl solution
  7. customthe residue was purified by flash column (ethyl acetate-heptane, v/v, 40%-60%)
  8. customyielded a slightly yellow solid

出典と根拠

ORDレコード
ord-20d9094c453d48b2ad5a1580a061e8aa
出典データセット
uspto-grants-2013_08
特許番号
US08519142B2

反応ノート

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