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

HRID 505540Notes

Reaction equation

HRID 505540 reaction equation
[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]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 79177tert-Butyl bromoacetateHCID 178509930HCID 178509930, compound

Product 1

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

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

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.

Workup

  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

Sources & evidence

ORD record
ord-4fbce000015b4b79a3eb5e234ee4265d
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

Loading…