Acetic Acid → HCID 86627515, compound

HRID 1970056Notes

Reaction equation

[I:1]Cl.[O:3]=[C:4]1[C:13]2[NH:14][CH:15]=[CH:16][C:12]=2[C:11]2[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=2[NH:5]1.[CH2:17]([C:19]([O-:21])=[O:20])[CH3:18].C(O)(=O)C.[O-]S(C(F)(F)F)(=O)=O.[In+3].[O-]S(C(F)(F)F)(=O)=O.[O-]S(C(F)(F)F)(=O)=O>ClCCl.C(#N)C>[I:1][C:9]1[CH:8]=[CH:7][C:6]2[NH:5][C:4](=[O:3])[C:13]3[NH:14][CH:15]=[CH:16][C:12]=3[C:11]=2[CH:10]=1.[CH2:17]([C:19]([O-:21])=[O:20])[CH3:18]

Participants

Conditions

Temperature: 45 °C

Procedure

Alternatively, 1.5 mL (1.5 mmol) of a 1M solution of iodine monochloride in dichloromethane is added to a solution of 316 mg (1 mmol) of 4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate cocrystallized with 1 equivalent of acetic acid and 652 mg (1 mmol) of indium triflate in anhydrous acetonitrile (20 mL). The solution is heated at 45° C. for 3 hours then stirred at room temperature for 20 hours. The solid is filtered, and triturated with acetonitrile and diisopropyl ether to give 368 mg (96%) of 8-iodo-4-oxo-4,5-dihydro-3H-pyrrolo[2,3-c]quinoline-1-ethyl carboxylate in the form of a white solid.

Workup

filtrationThe solid is filtered
customtriturated with acetonitrile and diisopropyl ether

Sources & evidence

ORD record: ord-7deac5343834438e96cd7cc680ff0514
Source dataset: uspto-grants-2013_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08426437B2

Reaction notes

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