Cesium carbonate → HCID 90418714, compound

HRID 513959Notes

Reaction equation

HRID 513959 reaction equation
Cl[CH2:2][C:3]1[CH:8]=[CH:7][N:6]=[C:5]([C:9]([F:12])([F:11])[F:10])[CH:4]=1.[OH:13][C:14]1[CH:23]=[C:22]2[C:17]([CH:18]=[C:19]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:20]=[N:21]2)=[CH:16][CH:15]=1.C([O-])([O-])=O.[Cs+].[Cs+]>CN(C=O)C>[F:10][C:9]([F:12])([F:11])[C:5]1[CH:4]=[C:3]([CH2:2][O:13][C:14]2[CH:23]=[C:22]3[C:17]([CH:18]=[C:19]([CH2:24][C:25]([O:27][CH2:28][CH3:29])=[O:26])[CH:20]=[N:21]3)=[CH:16][CH:15]=2)[CH:8]=[CH:7][N:6]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 104201934-ChloroMethyl-2-trifluoroMethyl-pyridineHCID 136629534HCID 136629534, compound2×

Product 1

HCID 90418714HCID 90418714, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-(chloromethyl)-2-(trifluoromethyl)pyridine (162.06 mg, 0.83 mmol) in DMF (5 mL) was added ethyl 2-(7-hydroxyquinolin-3-yl)acetate (Intermediate 2, 150 mg, 0.55 mmol) and Cs2CO3 (356 mg, 1.10 mmol). The reaction was stirred at ambient temperature for 16 h. A mixture of mono benzylated and bisbenzylated products were observed. Cesium carbonate was filtered off and DMF was removed under reduced pressure. Purification (FCC, SiO2, 0-50%, EtOAc/hexanes) afforded a mixture of methyl and ethyl esters along with 25% of bis-benzylated product. The mixture was advanced into the next reaction.

Workup

  1. additionA mixture
  2. filtrationCesium carbonate was filtered off
  3. customDMF was removed under reduced pressure
  4. customPurification (FCC, SiO2, 0-50%, EtOAc/hexanes)
  5. customafforded
  6. customThe mixture was advanced into the next reaction

Sources & evidence

ORD record
ord-08dc52ea77984562aac28d473c83404c
Source dataset
uspto-grants-2015_08
Patent number
US09102674B2

Reaction notes

Loading…