Cesium carbonate → HCID 90418714, compound

HRID 1748409Notes

Reaction equation

HRID 1748409 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-ae38cd90ed274b71b6155028ee5047ed
Source dataset
uspto-grants-2015_10
Patent number
US09150572B2

Reaction notes

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