Dimethylformamide → (5-bromo-2-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)thiophen-3-yl)(4-chlorophenyl)methanone

HRID 2401722ノート

反応式

HRID 2401722 の反応式
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:10]2[CH:14]=[CH:13][S:12][C:11]=2[C:15]2[N:19]=[CH:18][N:17]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][O:21]3)[N:16]=2)=[O:9])=[CH:4][CH:3]=1.CN(C)C=O.[Br:31]N1C(=O)CCC1=O>O.C(=O)(O)[O-].[Na+]>[Br:31][C:13]1[S:12][C:11]([C:15]2[N:19]=[CH:18][N:17]([CH:20]3[CH2:25][CH2:24][CH2:23][CH2:22][O:21]3)[N:16]=2)=[C:10]([C:8]([C:5]2[CH:6]=[CH:7][C:2]([Cl:1])=[CH:3][CH:4]=2)=[O:9])[CH:14]=1

参加物

6

反応物 3

HCID 6228Dimethylformamide2 回HCID 67184N-bromobutanimide2 回HCID 66749278(4-chlorophenyl)(2-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)thiophen-3-yl)methanone

生成物 1

HCID 66749271(5-bromo-2-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)thiophen-3-yl)(4-chlorophenyl)methanone

試薬・触媒・溶媒 2

HCID 962Water溶媒HCID 516892Sodium Bicarbonate溶媒

実験手順

To a mixture of (4-chlorophenyl){2-[1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl]-3-thienyl}methanone (20.2 g, 54.0 mmol) in N,N-dimethylformamide (350 mL, 4500 mmol) was added dropwise a solution of N-bromosuccinimide (14.42 g, 81.05 mmol) in N,N-dimethylformamide (50 mL, 600 mmol) under argon. The mixture was stirred at rt with care taken to block the reaction from exposure to ambient light. After 3 h reaction, LCMS showed both starting material and product. Additional N-bromosuccinimide (6.732 g, 37.82 mmol) was added and the mixture was stirred at rt again. After stirring overnight, the mixture was diluted with water and sodium bicarbonate solution and then the mixture was extracted with EtOAc. The organic layer was washed with water and brine. The EtOAc layer was dried and evaporated in vacuum to a residue, which was purified by chromatography to afford (5-bromo-2-(1-(tetrahydro-2H-pyran-2-yl)-1H-1,2,4-triazol-3-yl)thiophen-3-yl)(4-chlorophenyl)methanone as a white solid (18.0, 73.5%). LCMS: (FA) ES+ 451.9, 453.9

後処理

  1. customthe reaction from exposure to ambient light
  2. customAfter 3 h reaction, LCMS
  3. stirringthe mixture was stirred at rt again
  4. stirringAfter stirring overnight
  5. extractionthe mixture was extracted with EtOAc
  6. washThe organic layer was washed with water and brine
  7. dry with materialThe EtOAc layer was dried
  8. customevaporated in vacuum to a residue, which
  9. customwas purified by chromatography

出典と根拠

ORDレコード
ord-82666682053d44659504d3ff846c75f7
出典データセット
uspto-grants-2014_08
特許番号
US08796268B2

反応ノート

読み込み中…