Sodium hydride → HCID 59631129, compound

HRID 1431610Notes

Reaction equation

HRID 1431610 reaction equation
[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([N:14]2[CH2:19][CH2:18][NH:17][C:16](=[O:20])[CH2:15]2)[C:3]=1[CH3:21].[H-].[Na+].I[CH2:25][CH2:26][CH3:27]>C1COCC1>[Br:1][C:2]1[C:11]2[C:6](=[CH:7][C:8]([F:13])=[CH:9][C:10]=2[F:12])[N:5]=[C:4]([N:14]2[CH2:19][CH2:18][N:17]([CH2:25][CH2:26][CH3:27])[C:16](=[O:20])[CH2:15]2)[C:3]=1[CH3:21]

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 336431-IodopropaneHCID 59631383HCID 59631383, compound

Product 1

HCID 59631129HCID 59631129, compound

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

The 4-(4-bromo-5,7-difluoro-3-methylquinolin-2-yl)piperazin-2-one (70 mg, 0.200 mmol) was dissolved in THF (2.0 mL). To the solution was added sodium hydride (24.0 mg, 0.98 mmol) (60% dispersion) followed by addition of 1-iodopropane (230 μL, 2.40 mmol). The reaction was stirred overnight. The reaction was quenched with water and the mixture was extracted with EtOAc (2×50 mL). The combined organic layers were washed with brine (1×25 mL) and dried over magnesium sulfate. The crude product was purified by medium pressure chromatography (silica gel, 0 to 80% EtOAc:hexanes) to give 4-(4-bromo-5,7-difluoro-3-methylquinolin-2-yl)-1-propylpiperazin-2-one. Mass Spectrum (ESI) m/e=400.1 (M+1).

Workup

  1. customThe reaction was quenched with water
  2. extractionthe mixture was extracted with EtOAc (2×50 mL)
  3. washThe combined organic layers were washed with brine (1×25 mL)
  4. dry with materialdried over magnesium sulfate
  5. customThe crude product was purified by medium pressure chromatography (silica gel, 0 to 80% EtOAc:hexanes)

Sources & evidence

ORD record
ord-f7adb1dcbe594eb6a39a59e3df50a02f
Source dataset
uspto-grants-2015_01
Patent number
US08940724B2

Reaction notes

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