Ammonium Chloride → (S)-N-(5-bromo-6-(2-(3,5-difluorophenyl)-1-(1,1-dimethylethylsulfinamido)ethyl)pyridin-2-yl)acetamide

HRID 2170309

反応式

HRID 2170309 の反応式
[F:1][C:2]1[CH:3]=[C:4]([CH:8]=[C:9]([F:11])[CH:10]=1)[CH2:5][Mg]Br.[Br:12][C:13]1[CH:14]=[CH:15][C:16]([NH:27][C:28](=[O:30])[CH3:29])=[N:17][C:18]=1[CH:19]=[N:20][S@:21]([C:23]([CH3:26])([CH3:25])[CH3:24])=[O:22].[Cl-].[NH4+]>C(Cl)Cl>[Br:12][C:13]1[CH:14]=[CH:15][C:16]([NH:27][C:28](=[O:30])[CH3:29])=[N:17][C:18]=1[C@@H:19]([NH:20][S:21]([C:23]([CH3:25])([CH3:26])[CH3:24])=[O:22])[CH2:5][C:4]1[CH:3]=[C:2]([F:1])[CH:10]=[C:9]([F:11])[CH:8]=1

参加物

5

反応物 3

HCID 25517Ammonium ChlorideHCID 90280385(S)-N-(5-bromo-6-(((tert-butylsulfinyl)imino)methyl)pyridin-2-yl)acetamideHCID 178505920HCID 178505920、化合物

生成物 1

HCID 90280239(S)-N-(5-bromo-6-(2-(3,5-difluorophenyl)-1-(1,1-dimethylethylsulfinamido)ethyl)pyridin-2-yl)acetamide

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

反応条件

温度
-78 °C

実験手順

(3,5-Difluorobenzyl)magnesium bromide (0.25 M in ether, 10 ml, 2.5 mmol) was added dropwise to a solution of (S)—N-(5-bromo-6-(((tert-butylsulfinyl)imino)methyl)pyridin-2-yl)acetamide (1D, 0.47 g, 1.36 mmol) in DCM (5 ml) at 78° C. The reaction was stirred for 3 h at −78° C. Ammonium chloride (aq, 10 mL) was added to the reaction and the mixture was allowed to warm to r.t. The mixture was extracted with EtOAc (2×30 mL). The organic layer was dried over Na2SO4, filtered and concentrated. The crude product contained a mixture of diastereomers which were used in the next step without further purification. MS (m/z) 474.1 [M+H]+.

後処理

  1. temperatureto warm to r.t
  2. extractionThe mixture was extracted with EtOAc (2×30 mL)
  3. dry with materialThe organic layer was dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. additiona mixture of diastereomers which
  7. customwere used in the next step without further purification

出典と根拠

ORDレコード
ord-eadcb53de8e54fd991aca213f9a598d4
出典データセット
uspto-grants-2015_06
特許番号
US09050344B2

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