Iodine → HCID 86732561, compound

HRID 711412Notes

Reaction equation

HRID 711412 reaction equation
[I:1]I.[C:3]([O:7][C:8](=[O:33])[NH:9][CH2:10][CH2:11][CH:12]1[N:17]2[CH:18]=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]([F:31])([F:30])[F:29])[CH:22]=3)[CH:20]=[C:16]2[C:15](=[O:32])[NH:14][CH2:13]1)([CH3:6])([CH3:5])[CH3:4]>C(Cl)Cl.FC(F)(F)C([O-])=O.[Ag+]>[C:3]([O:7][C:8](=[O:33])[NH:9][CH2:10][CH2:11][CH:12]1[N:17]2[C:18]([I:1])=[C:19]([C:21]3[CH:26]=[CH:25][CH:24]=[C:23]([O:27][C:28]([F:29])([F:30])[F:31])[CH:22]=3)[CH:20]=[C:16]2[C:15](=[O:32])[NH:14][CH2:13]1)([CH3:6])([CH3:4])[CH3:5]

Participants

5

Reactant 2

HCID 807IodineHCID 89493856HCID 89493856, compound

Product 1

HCID 86732561HCID 86732561, compoundYield 99.9%

Reagents, catalysts & solvents 2

HCID 76299Silver trifluoroacetateCatalystHCID 6344DichloromethaneSolvent

Procedure

Iodine (450 mg 1.77 mmol) was added portion wise to a solution of tert-butyl(2-{1-oxo-7-[3-(trifluoromethoxy)phenyl]-1,2,3,4-tetrahydropyrrolo[1,2-a]pyrazin-4-yl}ethyl)carbamate (780 mg 1.77 mmol) and silver trifluoroacetate (392 mg, 1.77 mmol) in dry DCM (100 ml), at 5° C. The reaction mixture was stirred at the same temperature for 1 hour, then the ice bath removed and left to warm to rt (1 h). The solid was filtered, the organic phase washed with Na2S2O5 (5% aq. solution) until decolouration occurred and finally washed with water. The organic was dried over Na2SO4 to obtain the title compound 1.0 g (99%) as a white solid.

Workup

  1. customat 5° C
  2. customthe ice bath removed
  3. waitleft
  4. filtrationThe solid was filtered
  5. washthe organic phase washed with Na2S2O5 (5% aq. solution) until decolouration
  6. washfinally washed with water
  7. dry with materialThe organic was dried over Na2SO4

Sources & evidence

ORD record
ord-429470dba2f64249ba796811a2456e8d
Source dataset
uspto-grants-2015_11
Patent number
US09181258B2

Reaction notes

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