Benzyl Bromide → HCID 67107295, compound

HRID 1623826Notes

Reaction equation

HRID 1623826 reaction equation
C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:7](Br)[C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1.[OH:15][C:16]1[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:18][C:17]=1[C:29]([NH:31][C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1)=[O:30].C(OCC)(=O)C>CN(C)C=O.O>[C:8]1([CH2:7][O:15][C:16]2[CH:21]=[CH:20][C:19]([CH2:22][CH2:23][C:24]([O:26][CH2:27][CH3:28])=[O:25])=[CH:18][C:17]=2[C:29]([NH:31][C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)=[O:30])[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 8857Ethyl AcetateHCID 10796Cesium carbonateHCID 67108014HCID 67108014, compound

Product 1

HCID 67107295HCID 67107295, compound

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Procedure

Cesium carbonate (171 mg, 0.53 mmol) and benzyl bromide (0.05 ml, 0.42 mmol) were added to a solution of ethyl 3-{4-hydroxy-3-[(3-pyridinylamino)carbonyl]phenyl}propanoate (may be prepared as described in Description 98; 110 mg, 0.35 mmol) in N,N-dimethylformamide (10 ml). The mixture was stirred for one hour and then ethyl acetate (10 ml) and water (10 ml) were added. The organic layer was separated, washed further with water (3×10 ml), dried (MgSO4) and the solvent removed in vacuo to yield the title compound as a yellow solid. 126 mg.

Workup

  1. customThe organic layer was separated
  2. washwashed further with water (3×10 ml)
  3. dry with materialdried (MgSO4)
  4. customthe solvent removed in vacuo

Sources & evidence

ORD record
ord-4261b4fdcb57402589061880714f5ac0
Source dataset
uspto-grants-2014_07
Patent number
US08778939B2

Reaction notes

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