tert-butyl 7-bromo-2-(4-methoxybenzyl)-3-oxo-2',3'-dihydro-1'H-spiro[isoindoline-1,4'-pyridine]-1'-carboxylate → 7-bromo-2',3'-dihydro-1'H-spiro[isoindoline-1,4'-pyridin]-3-one

HRID 390137Notes

Reaction equation

HRID 390137 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:22]=1[C:9]1([CH:14]=[CH:13][N:12](C(OC(C)(C)C)=O)[CH2:11][CH2:10]1)[N:8](CC1C=CC(OC)=CC=1)[C:7]2=[O:32]>C(O)(C(F)(F)F)=O.C(S(O)(=O)=O)(F)(F)F>[Br:1][C:2]1[CH:3]=[CH:4][CH:5]=[C:6]2[C:22]=1[C:9]1([CH:10]=[CH:11][NH:12][CH2:13][CH2:14]1)[NH:8][C:7]2=[O:32]

Participants

4

Reactant 1

HCID 58295753tert-butyl 7-bromo-2-(4-methoxybenzyl)-3-oxo-2',3'-dihydro-1'H-spiro[isoindoline-1,4'-pyridine]-1'-carboxylate

Product 1

HCID 582957447-bromo-2',3'-dihydro-1'H-spiro[isoindoline-1,4'-pyridin]-3-oneYield 72%

Reagents, catalysts & solvents 2

HCID 6422Trifluoroacetic acidSolventHCID 62406Trifluoromethanesulfonic acidSolvent

Procedure

A solution of tert-butyl 7-bromo-2-(4-methoxybenzyl)-3-oxo-2′,3′-dihydro-1′H-spiro[isoindoline-1,4′-pyridine]-1′-carboxylate (5 g, 0.01 mol) in TFA (50 mL) and CF3SO3H (5 mL) was stirred and heated for 8 h. The mixture was concentrated to give a residue which was washed with aq NaOH and extracted with EtOAc. The organic layer was dried and concentrated to give 7-bromo-2′,3′-dihydro-1′H-spiro[isoindoline-1,4′-pyridin]-3-one (2.0 g, 72%).

Workup

  1. temperatureheated for 8 h
  2. concentrationThe mixture was concentrated
  3. customto give a residue which
  4. washwas washed with aq NaOH
  5. extractionextracted with EtOAc
  6. customThe organic layer was dried
  7. concentrationconcentrated

Sources & evidence

ORD record
ord-55737638758e4c0481ac390b41f6be41
Source dataset
uspto-grants-2013_02
Patent number
US08383629B2

Reaction notes

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