Trifluoroacetic acid → 5-Cyanoisoindoline trifluoroacetate

HRID 268714Notes

Reaction equation

HRID 268714 reaction equation
C(OC([N:8]1[CH2:16][C:15]2[C:10](=[CH:11][CH:12]=[C:13]([C:17]#[N:18])[CH:14]=2)[CH2:9]1)=O)(C)(C)C.[C:19]([OH:25])([C:21]([F:24])([F:23])[F:22])=[O:20]>C(Cl)Cl>[F:22][C:21]([F:24])([F:23])[C:19]([OH:25])=[O:20].[C:17]([C:13]1[CH:14]=[C:15]2[C:10](=[CH:11][CH:12]=1)[CH2:9][NH:8][CH2:16]2)#[N:18]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 18630967tert-Butyl 5-cyano-1,3-dihydro-2H-isoindole-2-carboxylate

Product 1

HCID 179862795-Cyanoisoindoline trifluoroacetate

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of N-t-butoxycarbonyl-5-cyanoisoindoline (D15) (130 mg) in DCM (3 ml) at rt was treated with TFA (1 ml) and after 1 h it was evaporated. The residue was re-evaporated from MeOH/toluene to give the title compound (D16) (140 mg). 1H NMR δ (CDCl3): 7.70 (2H, m), 7.50 (1H, m), 4.75 (4H, m).

Workup

  1. customwas evaporated
  2. customThe residue was re-evaporated from MeOH/toluene

Sources & evidence

ORD record
ord-23a5ec05c1184be59fb21a0ec0c3e633
Source dataset
uspto-grants-2008_11
Patent number
US07446103B2

Reaction notes

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