Cesium carbonate → HCID 67376135, compound

HRID 522881Notes

Reaction equation

HRID 522881 reaction equation
[OH:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2.C(=O)([O-])[O-].[Cs+].[Cs+].FC(F)(F)S(O[CH2:31][C:32]([F:35])([F:34])[F:33])(=O)=O>CN(C=O)C>[F:33][C:32]([F:35])([F:34])[CH2:31][O:1][C:2]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[CH2:4][CH2:5][N:6]([C:12]([O:14][C:15]([CH3:18])([CH3:17])[CH3:16])=[O:13])[CH2:7]2

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 803662,2,2-Trifluoroethyl trifluoromethanesulfonateHCID 10538586tert-Butyl 5-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate

Product 1

HCID 67376135HCID 67376135, compoundYield 45.2%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
70 °C

Procedure

To a resealable tube was added tert-butyl 5-hydroxy-3,4-dihydroisoquinoline-2(1H)-carboxylate (200 mg, 0.802 mmol) and cesium carbonate (601 mg, 1.845 mmol) in DMF (2 mL) followed by 2,2,2-trifluoroethyl trifluoromethanesulfonate (1005 mg, 4.33 mmol). The reaction mixture stirred at 70° C. overnight. The crude material was purified by reverse-phase preparative HPLC using 0.1% TFA in CH3CN/H2O, gradient 55% to 95% over 10 min to provide tert-butyl 5-(2,2,2-trifluoroethoxy)-3,4-dihydroisoquinoline-2(1H)-carboxylate (120 mg) as colorless oil.

Workup

  1. customThe crude material was purified by reverse-phase preparative HPLC
  2. customover 10 min

Sources & evidence

ORD record
ord-caf1accc421546b3b2c148d691dda487
Source dataset
uspto-grants-2016_05
Patent number
US09334269B2

Reaction notes

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