Cesium carbonate → tert-Butyl[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]acetate

HRID 505540ノート

反応式

HRID 505540 の反応式
[Cl:1][C:2]1[CH:3]=[C:4]([CH:7]=[C:8]([O:10][C:11]2[C:19]3[N:18]=[N:17][NH:16][C:15]=3[CH:14]=[CH:13][C:12]=2[Cl:20])[CH:9]=1)[C:5]#[N:6].C(=O)([O-])[O-].[Cs+].[Cs+].Br[CH2:28][C:29]([O:31][C:32]([CH3:35])([CH3:34])[CH3:33])=[O:30]>CN(C=O)C>[C:32]([O:31][C:29](=[O:30])[CH2:28][N:16]1[C:15]2[CH:14]=[CH:13][C:12]([Cl:20])=[C:11]([O:10][C:8]3[CH:7]=[C:4]([C:5]#[N:6])[CH:3]=[C:2]([Cl:1])[CH:9]=3)[C:19]=2[N:18]=[N:17]1)([CH3:35])([CH3:34])[CH3:33]

参加物

5

反応物 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 178509930HCID 178509930、化合物

生成物 1

HCID 86624476tert-Butyl[5-chloro-4-(3-chloro-5-cyanophenoxy)-1H-1,2,3-benzotriazol-1-yl]acetate

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

3-chloro-5-[(5-chloro-1H-1,2,3-benzotriazol-4-yl)oxy]benzonitrile (500 mg, 1.64 mmol) and cesium carbonate (534 mg, 1.64 mmol) were suspended in DMF (5 mL) under N2. To this was added tert-butyl bromoacetate (336 mg, 1.72 mmol) After 1 hour, the reaction was quenched with saturated aqueous ammonium chloride (5 mL), diluted with water and the mixture extracted with ethyl acetate (2×25 mL). The combined organic fractions were washed with water (3×25 mL) and dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by automated column chromatography on silica gel (40 g) eluting with 0-15% EtOAc/hexanes to give the title product. LRMS (M+1)=418.9.

後処理

  1. customthe reaction was quenched with saturated aqueous ammonium chloride (5 mL)
  2. additiondiluted with water
  3. extractionthe mixture extracted with ethyl acetate (2×25 mL)
  4. washThe combined organic fractions were washed with water (3×25 mL)
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. customthe solvent was evaporated under reduced pressure
  8. customThe resulting residue was purified by automated column chromatography on silica gel (40 g)
  9. washeluting with 0-15% EtOAc/hexanes

出典と根拠

ORDレコード
ord-4fbce000015b4b79a3eb5e234ee4265d
出典データセット
uspto-grants-2010_08
特許番号
US07781454B2

反応ノート

読み込み中…