Cesium carbonate → HCID 10272253, compound

HRID 1057370Notes

Reaction equation

HRID 1057370 reaction equation
[C:1]([O:5][C:6]([CH:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:11]=2[NH:10][C:9]1=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2].[F:22][C:23]1[CH:24]=[C:25]([CH:28]=[CH:29][CH:30]=1)[CH2:26]Br.C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[C:1]([O:5][C:6]([CH:8]1[CH2:14][CH2:13][C:12]2[CH:15]=[CH:16][C:17]([O:19][CH3:20])=[CH:18][C:11]=2[N:10]([CH2:26][C:25]2[CH:28]=[CH:29][CH:30]=[C:23]([F:22])[CH:24]=2)[C:9]1=[O:21])=[O:7])([CH3:4])([CH3:3])[CH3:2]

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 680073-Fluorobenzyl bromideHCID 9857210HCID 9857210, compound

Product 1

HCID 10272253HCID 10272253, compoundYield 77%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

A suspension of 3-tert-butoxycarbonyl-8-methoxy-2,3,4,5-tetrahydro-1H-1-benzazepine-2-one (2.0 g, 6.86 mmol), 3-fluorobenzyl bromide (1.68 mL, 13.72 mmol) and Cs2CO3 (4.48 g, 13.72 mmol) in acetonitrile (20 mL) was stirred at room temperature for 16 hours. The reaction mixture was evaporated to dryness, the residue dissolved in water and extracted with DCM. The organic layer was washed with water, dried over Na2SO4, filtered and evaporated to dryness. Thus obtained crude product was purified by flash chromatography on silica gel column eluted with ethyl acetate/n-hexane (30% of ethyl acetate in n-hexane). The title compound (2.10 g, 77%) was obtained as a colorless foam.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. dissolutionthe residue dissolved in water
  3. extractionextracted with DCM
  4. washThe organic layer was washed with water
  5. dry with materialdried over Na2SO4
  6. filtrationfiltered
  7. customevaporated to dryness
  8. customThus obtained crude product
  9. customwas purified by flash chromatography on silica gel column
  10. washeluted with ethyl acetate/n-hexane (30% of ethyl acetate in n-hexane)

Sources & evidence

ORD record
ord-2690e8255d4341f0bb75e00bda7d15b2
Source dataset
uspto-grants-2003_02
Patent number
US06514965B1

Reaction notes

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