Ethyl bromoacetate → HCID 58562908, compound

HRID 2175523Notes

Reaction equation

HRID 2175523 reaction equation
[F:1][C:2]([F:25])([F:24])[C:3]1[CH:4]=[C:5]2[C:10](=[CH:11][CH:12]=1)[N:9]=[CH:8][CH:7]=[C:6]2[NH:13][C:14](=[O:23])[O:15][CH2:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:32]([O:34][C:35](=[O:38])[CH2:36]Br)[CH3:33].[NH4+].[Cl-]>CN(C=O)C>[CH2:16]([O:15][C:14]([N:13]([C:6]1[C:5]2[C:10](=[CH:11][CH:12]=[C:3]([C:2]([F:1])([F:24])[F:25])[CH:4]=2)[N:9]=[CH:8][CH:7]=1)[CH2:36][C:35]([O:34][CH2:32][CH3:33])=[O:38])=[O:23])[C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1

Participants

6

Reactant 4

HCID 7748Ethyl bromoacetateHCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 58562610HCID 58562610, compound

Product 1

HCID 58562908HCID 58562908, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

A solution of benzyl (6-(trifluoromethyl)quinolin-4-yl)carbamate (440 mg, 1.27 mmol, prepared in Step D) in dry DMF (20 mL) is treated with cesium carbonate (870 mg, 2.67 mmol) and stirred at room temperature for 1 hour. Ethylbromoacetate (0.15 mL, 1.36 mmol) is added dropwise and the reaction mixture is stirred at room temperature overnight. The reaction mixture was then poured into saturated NH4Cl solution and extracted with ethyl acetate. After concentration in vacuo, the residue was purified by flash chromatography (silica gel, 0-100% ethyl acetate/DCM) to afford the title compound.

Workup

  1. stirringthe reaction mixture is stirred at room temperature overnight
  2. extractionextracted with ethyl acetate
  3. concentrationAfter concentration in vacuo
  4. customthe residue was purified by flash chromatography (silica gel, 0-100% ethyl acetate/DCM)

Sources & evidence

ORD record
ord-e44ca0b325d94c89a1822eeac3258c4a
Source dataset
uspto-grants-2015_06
Patent number
US09062048B2

Reaction notes

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