Benzyl Bromide → HCID 22724251, compound

HRID 2086883Notes

Reaction equation

HRID 2086883 reaction equation
[CH2:1]([C:8]1[C:13](=[O:14])[N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([OH:23])=[O:22])[CH:16]=2)[C:11]2[N:24]=[CH:25][CH:26]=[CH:27][C:10]=2[N:9]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1.C(=O)([O-])[O-].[K+].[K+].C(=O)(O)[O-].[Na+]>CN(C)C=O.C(OCC)(=O)C>[CH2:1]([C:8]1[C:13](=[O:14])[N:12]([C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([C:21]([O:23][CH2:28][C:29]3[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=3)=[O:22])[CH:16]=2)[C:11]2[N:24]=[CH:25][CH:26]=[CH:27][C:10]=2[N:9]=1)[C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=1

Participants

7

Reactant 4

HCID 7498Benzyl BromideHCID 11430Potassium CarbonateHCID 516892Sodium BicarbonateHCID 22724010HCID 22724010, compound

Product 1

HCID 22724251HCID 22724251, compoundYield 82.3%

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-benzyl-4-(3-carboxyphenyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (200 mg), benzyl bromide (144 mg) and potassium carbonate (155 mg) in N,N-dimethylformamide (2 ml) was stirred at room temperature for 1 hour. Then the mixture was poured into a mixture of ethyl acetate and aqueous sodium bicarbonate. The organic phase was separated, washed with aqueous sodium bicarbonate and brine, dried over magnesium sulfate and concentrated. The resultant solid was collected and washed with isopropyl ether to give 2-benzyl-4-(3-benzyloxycarbonylphenyl)-3-oxo-3,4-dihydropyrido[2,3-b]pyrazine (206 mg).

Workup

  1. customThe organic phase was separated
  2. washwashed with aqueous sodium bicarbonate and brine
  3. dry with materialdried over magnesium sulfate
  4. concentrationconcentrated
  5. customThe resultant solid was collected
  6. washwashed with isopropyl ether

Sources & evidence

ORD record
ord-58dee35f5bec4f2296dafc33bfab2d35
Source dataset
uspto-grants-2004_04
Patent number
US06727245B2

Reaction notes

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