Cesium carbonate → 3-chloro-5-({5-chloro-1-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]-1H-1,2,3-benzotriazol-4-yl}oxy)benzonitrile

HRID 505558Notes

Reaction equation

HRID 505558 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+].Cl[CH2:28][C:29]1[O:30][C:31]([C:34]2[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=2)=[N:32][N:33]=1>CN(C=O)C>[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][N:16]([CH2:28][C:29]4[O:30][C:31]([C:34]5[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=5)=[N:32][N:33]=4)[C:15]=3[CH:14]=[CH:13][C:12]=2[Cl:20])[CH:9]=1)[C:5]#[N:6]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 3149412-(Chloromethyl)-5-phenyl-1,3,4-oxadiazoleHCID 178509930HCID 178509930, compound

Product 1

HCID 684276303-chloro-5-({5-chloro-1-[(5-phenyl-1,3,4-oxadiazol-2-yl)methyl]-1H-1,2,3-benzotriazol-4-yl}oxy)benzonitrile

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

3-chloro-5-[(5-chloro-1H-1,2,3-benzotriazol-4-yl)oxy]benzonitrile (100 mg, 0.328 mmol), cesium carbonate (107 mg, 0.328 mmol) and 2-(chloromethyl)-5-phenyl-1,3,4-oxadiazole (64 mg, 0.328 mmol) were combined and suspended in DMF (2 mL). After 16 hours at room temperature, the reaction mixture was quenched with saturated aqueous ammonium chloride (1 mL) and extracted with EtOAc (2×25 mL). The combined organic fractions were evaporated under reduced pressure, and the resulting residue was purified by reverse phase chromatography eluting with 30-95% MeCN/H2O+0.1% TFA. The product fractions were concentrated to yield the title compound. 1H NMR (DMSO-d6) δ 8.01 (d, J=8.9 Hz, 1H), 7.96 (d, J=8.3 Hz, 2H), 7.88 (d, J=8.9 Hz, 1H), 7.83 (m, 1H), 7.61 (m, 5H), 6.54 (s, 2H). HRMS (M+1)=463.0465.

Workup

  1. customthe reaction mixture was quenched with saturated aqueous ammonium chloride (1 mL)
  2. extractionextracted with EtOAc (2×25 mL)
  3. customThe combined organic fractions were evaporated under reduced pressure
  4. customthe resulting residue was purified by reverse phase chromatography
  5. washeluting with 30-95% MeCN/H2O+0.1% TFA
  6. concentrationThe product fractions were concentrated

Sources & evidence

ORD record
ord-7f41014884d44382a947c3cfeeb5303e
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

Loading…