Benzyl Bromide → HCID 18705806, compound

HRID 2287836Notes

Reaction equation

HRID 2287836 reaction equation
[H-].[Na+].[F:3][C:4]([F:27])([F:26])[S:5]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[OH:18])[CH2:14][CH:13]([N:19]([CH2:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22])[CH2:12]2)(=[O:7])=[O:6].[CH2:28](Br)[C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1>CCCCCC.CN(C=O)C>[F:27][C:4]([F:26])([F:3])[S:5]([O:8][C:9]1[CH:10]=[C:11]2[C:15](=[CH:16][C:17]=1[O:18][CH2:28][C:29]1[CH:34]=[CH:33][CH:32]=[CH:31][CH:30]=1)[CH2:14][CH:13]([N:19]([CH2:23][CH2:24][CH3:25])[CH2:20][CH2:21][CH3:22])[CH2:12]2)(=[O:6])=[O:7]

Participants

6

Reactant 3

HCID 7498Benzyl BromideHCID 24758Sodium hydrideHCID 18705875HCID 18705875, compound

Product 1

HCID 18705806HCID 18705806, compound

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolvent3×HCID 8058HexaneSolvent

Procedure

Sodium hydride (0.96 g, 24 mmol) was washed with hexane under nitrogen and suspended in DMF (10 mL). 2-(Dipropylamino)-2,3-dihydro-6-hydroxy-1H-inden-5-yl trifluoromethanesulfonate (69, 7.6 g, 20 mmol) in DMF (30 mL) was added dropwise at 0-5° C. over 30 min and the mixture stirred 30 min. Benzyl bromide (5.13 g, 30 mmol) in DMF (5 mL) was added and the resulting mixture was stirred 1 h. The reaction was quenched with saturated NaHCO3 and extracted with EtOAc. The organic layer was washed with water, brine, dried (MgSO4), filtered and concentrated to give the crude product. Chromatographic purification yielded pure product 70 as an oil that was converted into the HCl salt and crystallized from EtOAc/MeOH/hexane to give a white solid (mp 162-163° C.).

Workup

  1. stirringthe resulting mixture was stirred 1 h
  2. customThe reaction was quenched with saturated NaHCO3
  3. extractionextracted with EtOAc
  4. washThe organic layer was washed with water, brine
  5. dry with materialdried (MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customto give the crude product
  9. customChromatographic purification

Sources & evidence

ORD record
ord-c425d38d51a04f9093ee22d7cbe1c95f
Source dataset
uspto-grants-2000_07
Patent number
US06084130

Reaction notes

Loading…