HCID 58910028, compound → HCID 22929848, compound

HRID 1295926Notes

Reaction equation

HRID 1295926 reaction equation
[Br:1][CH2:2][C:3]1[C:19]([C:20]#[N:21])=[CH:18][C:6]([C:7]([N:9](C)[C:10](=O)OC(C)(C)C)=[O:8])=[C:5]([O:22][CH2:23][CH3:24])[CH:4]=1>ClCCl.FC(F)(F)C(O)=O>[CH3:10][NH:9][C:7](=[O:8])[C:6]1[CH:18]=[C:19]([C:20]#[N:21])[C:3]([CH2:2][Br:1])=[CH:4][C:5]=1[O:22][CH2:23][CH3:24]

Participants

4

Reactant 1

HCID 58910028HCID 58910028, compound

Product 1

HCID 22929848HCID 22929848, compoundYield 66.2%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Procedure

After dissolving tert-butyl N-[4-(bromomethyl)-5-cyano-2-ethoxybenzoyl]-N-methylcarbamate (39.9 g) in dichloromethane (300 ml), trifluoroacetic acid (50 ml) was added and the mixture was stirred at room temperature for 30 minutes. The reaction mixture was concentrated and the residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate) to yield the title compound (19.77 g) as a white solid.

Workup

  1. additionwas added
  2. concentrationThe reaction mixture was concentrated
  3. customthe residue was purified by silica gel column chromatography (solvent: n-hexane-ethyl acetate)

Sources & evidence

ORD record
ord-7a61708904724355b3082024bbb79ca3
Source dataset
uspto-grants-2007_07
Patent number
US07244730B2

Reaction notes

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