Cesium carbonate → HCID 25109751, compound

HRID 505535Notes

Reaction equation

HRID 505535 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]([C:31]1[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=1)=[O:30]>CN(C=O)C.O>[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](=[O:30])[C:31]4[CH:32]=[N:33][CH:34]=[CH:35][CH:36]=4)[C:15]=3[CH:14]=[CH:13][C:12]=2[Cl:20])[CH:9]=1)[C:5]#[N:6]

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 1514083-(2-Bromoacetyl)pyridineHCID 178509930HCID 178509930, compound

Product 1

HCID 25109751HCID 25109751, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

3-chloro-5-[(5-chloro-1H-1,2,3-benzotriazol-4-yl)oxy]benzonitrile (50 mg, 0.164 mmol) and cesium carbonate (160 mg, 0.492 mmol) were suspended in DMF (1 μL) at room temperature under N2. To this was added 2-bromo-1-pyridin-3-ylethanone (48.3 mg, 0.172 mmol) as a solid. The resulting mixture was stirred under N2 for 16 hours. The reaction mixture was then diluted with water (2 mL) and extracted with EtOAc (2×15 mL). The combined organic fractions were washed with water (3×10 mL), dried (MgSO4), filtered and the solvent was evaporated under reduced pressure. The resulting residue was purified by reverse phase chromatography eluting with 30-95% MeCN/H2O+0.1% TFA. The product was lyophilized to afford the title compound. 1H NMR (DMSO-d6) δ 9.30 (s, 1H), 8.90 (m, 1H), 8.44 (d, J=7.8 Hz, 1H), 7.88 (d, J=8.8 Hz, 1H), 7.85 (m, 1H), 7.79 (d, J=8.8 Hz, 1H), 7.68 (m, 1H), 7.60 (m, 1H), 7.57 (m, 1H), 6.68 (s, 2H). HRMS (M+1)=424.0395

Workup

  1. extractionextracted with EtOAc (2×15 mL)
  2. washThe combined organic fractions were washed with water (3×10 mL)
  3. dry with materialdried (MgSO4)
  4. filtrationfiltered
  5. customthe solvent was evaporated under reduced pressure
  6. customThe resulting residue was purified by reverse phase chromatography
  7. washeluting with 30-95% MeCN/H2O+0.1% TFA

Sources & evidence

ORD record
ord-daa0042a66ba44119851b3509b1bd9dc
Source dataset
uspto-grants-2010_08
Patent number
US07781454B2

Reaction notes

Loading…