Ethyl bromoacetate → HCID 58562908, compound

HRID 1896840Notes

Reaction equation

HRID 1896840 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-2659aa468e3b4f479f97c4c8f2aab46b
Source dataset
uspto-grants-2013_08
Patent number
US08518969B2

Reaction notes

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