Tetra-n-butylammonium tribromide → HCID 59846182, compound

HRID 1697080Notes

Reaction equation

HRID 1697080 reaction equation
[Br-:1].[Br-].[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.C([N+](CCCC)(CCCC)CCCC)CCC.[CH3:55][O:56][C:57]([C:59]1[N:60]([C:81]2[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=2)[C:61]2[C:66]([C:67](=[O:79])[C:68]=1[CH2:69][C:70]1[CH:75]=[CH:74][C:73]([C:76](=[O:78])[CH3:77])=[CH:72][CH:71]=1)=[CH:65][CH:64]=[C:63]([CH3:80])[N:62]=2)=[O:58]>CO>[CH3:55][O:56][C:57]([C:59]1[N:60]([C:81]2[CH:86]=[CH:85][CH:84]=[CH:83][CH:82]=2)[C:61]2[C:66]([C:67](=[O:79])[C:68]=1[CH2:69][C:70]1[CH:75]=[CH:74][C:73]([C:76](=[O:78])[CH2:77][Br:1])=[CH:72][CH:71]=1)=[CH:65][CH:64]=[C:63]([CH3:80])[N:62]=2)=[O:58]

Participants

4

Reactant 2

HCID 23500184Tetra-n-butylammonium tribromideHCID 59846257HCID 59846257, compound

Product 1

HCID 59846182HCID 59846182, compound

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

Tetrabutylammonium tribromide (72 mg, 0.15 mmol) was added to a solution of 3-(4-acetylbenzyl)-7-methyl-4-oxo-1-phenyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester (53 mg, 0.12 mmol) in MeOH (8 mL), and the resulting mixture stirred at RT overnight. The reaction mixture was concentrated under reduced pressure, and the crude residue purified by preparative TLC (EtOAc/hexane, 10/90) to afford 23 of 3-[4-(2-bromoacetyl)-benzyl]-7-methyl-4-oxo-1-phenyl-1,4-dihydro-[1,8]naphthyridine-2-carboxylic acid methyl ester as an off-white powder. MS=507 [M+H]+; MP=189.0-191.1° C.

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe crude residue purified by preparative TLC (EtOAc/hexane, 10/90)

Sources & evidence

ORD record
ord-194b063c87b9400fa9e07f7a69f40de4
Source dataset
uspto-grants-2012_04
Patent number
US08163906B2

Reaction notes

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