Methyl 3-bromopropanoate → HCID 21699804, compound

HRID 618171Notes

Reaction equation

HRID 618171 reaction equation
[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][N:9]=2)[CH:4]=[CH:3][CH:2]=1.[CH3:11][Si]([N-][Si](C)(C)C)(C)C.[Na+].Br[CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25]>C1COCC1>[N:1]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][N:9]=2)[C:4]([CH2:11][CH2:22][CH2:23][C:24]([O:26][CH3:27])=[O:25])=[CH:3][CH:2]=1

Participants

5

Reactant 3

HCID 76934Methyl 3-bromopropanoateHCID 1360691,8-NaphthyridineHCID 2724254Sodium bis(trimethylsilyl)amide

Product 1

HCID 21699804HCID 21699804, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a stirred solution of naphthyridine 23-1 (Hamada, Y. et al., Chem. Pharm. Bull. Soc., 1971, 19(9), 1857-1862), (2.2 g, 15.2 mmol) and THF (200 ml) at -78° C. was added NaN(TMS)2 (1M/THF, 18 ml, 18 mmol) dropwise over a 20 min period. After 30 minutes at -78° C., methyl 3-bromopropionate was added in a stream. After 30 min, the reaction was quenched with 50 ml 10% KHSO4. The mixture was extracted with Et2O. The remaining aqueous portion was basified with sat. NaHCO3 and then extracted with EtOAc. The EtOAc portion was washed with brine, dried (MgSO4) and concentrated. Flash chromatography (silica, 2% EtOH/EtOAc) gave the ester 23-2 (1.61 g) as a yellow oil.

Workup

  1. waitAfter 30 min
  2. customthe reaction was quenched with 50 ml 10% KHSO4
  3. extractionThe mixture was extracted with Et2O
  4. extractionextracted with EtOAc
  5. washThe EtOAc portion was washed with brine
  6. dry with materialdried (MgSO4)
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-bf25b407225c42a1a290ba4a7fd71e2f
Source dataset
uspto-grants-1999_09
Patent number
US05952306

Reaction notes

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