Trifluoroacetic acid → HCID 58266511, compound

HRID 1888501Notes

Reaction equation

HRID 1888501 reaction equation
FC(F)(F)C(O)=O.C(OC(=O)[NH:14][C:15]1[CH:16]=[N:17][C:18]([Cl:23])=[C:19]([Br:22])[C:20]=1[I:21])(C)(C)C>C(Cl)Cl>[Br:22][C:19]1[C:20]([I:21])=[C:15]([NH2:14])[CH:16]=[N:17][C:18]=1[Cl:23]

Participants

4

Reactant 2

HCID 6422Trifluoroacetic acidHCID 58266327HCID 58266327, compound

Product 1

HCID 58266511HCID 58266511, compoundYield 78.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

Trifluoroacetic acid (30 mL) was added to a solution of (5-bromo-6-chloro-4-iodo-pyridin-3-yl)-carbamic acid tert-butyl ester (19.0 g, 44 mmol) in DCM (120 mL) and the resultant solution was stirred at ambient temperature for 2 h then concentrated in vacuo. The resultant residue was loaded onto an SCX-2 cartridge (70 g) eluting with acetonitrile (100 mL) then 2N ammonia in methanol (100 mL). The basic fraction was concentrated in vacuo to afford the title compound (11.5 g, 78%). 1H NMR (DMSO-D6, 400 MHz): 7.23 (s, 1H), 5.92 (s, 2H).

Workup

  1. concentrationthen concentrated in vacuo
  2. washeluting with acetonitrile (100 mL)
  3. concentrationThe basic fraction was concentrated in vacuo

Sources & evidence

ORD record
ord-c199e2bf50164c4d8a4b0c6f5b8d580e
Source dataset
uspto-grants-2013_08
Patent number
US08501765B2

Reaction notes

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