Sodium hydride → HCID 9948742, compound

HRID 1761009Notes

Reaction equation

HRID 1761009 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[NH:11][CH2:10]2.[H-].[Na+].Br[CH2:23][C:24]([NH2:26])=[O:25]>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([CH:17]=[CH:18][CH:19]=1)[CH2:5][O:6][C:7]1[CH:8]=[C:9]2[C:13](=[CH:14][CH:15]=1)[C:12](=[O:16])[N:11]([CH2:23][C:24]([NH2:26])=[O:25])[CH2:10]2

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 696322-BromoacetamideHCID 22594218HCID 22594218, compound

Product 1

HCID 9948742HCID 9948742, compoundYield 67%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

A mixture of 5-(3-fluoro-benzyloxy)-2,3-dihydro-isoindol-1-one (400 mg, 1.6 mmol), sodium hydride (55% in mineral oil, 75 mg, 1.7 mmol) in THF (20 mL) was stirred at RT for 45 min, and then 2-bromoacetamide (75 mg, 1.9 mmol) was added and the resulting mixture heated at 50° C. for 16 h. After cooling to RT the mixture was half-evaporated and diluted with water. The mixture was extracted with ethyl acetate and the combined organic layers were washed with brine and dried over sodium sulfate. After filtration and evaporation the residue was purified by chromatography (SiO2, CH2Cl2:2N NH3-MeOH 98:2 to 85:15) to afford the title product (337 mg, 67%) as a white solid. MS m/e=315.3 (M+H+).

Workup

  1. temperaturethe resulting mixture heated at 50° C. for 16 h
  2. temperatureAfter cooling to RT the mixture
  3. customwas half-evaporated
  4. additiondiluted with water
  5. extractionThe mixture was extracted with ethyl acetate
  6. washthe combined organic layers were washed with brine
  7. dry with materialdried over sodium sulfate
  8. filtrationAfter filtration and evaporation the residue
  9. customwas purified by chromatography (SiO2, CH2Cl2:2N NH3-MeOH 98:2 to 85:15)

Sources & evidence

ORD record
ord-8891dcf69f674268ae93ad24b27e73b9
Source dataset
uspto-grants-2005_01
Patent number
US06846832B2

Reaction notes

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