Trifluoroacetic acid → HCID 68488661, compound

HRID 21242Notes

Reaction equation

HRID 21242 reaction equation
O[CH:2]1[C:10]2[C:5](=[C:6]([I:13])[CH:7]=[C:8]([F:12])[C:9]=2[Cl:11])[C:4](=[O:14])[N:3]1C(C)(C1C=CC=CC=1)C.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>[N+](C)([O-])=O>[Cl:11][C:9]1[C:8]([F:12])=[CH:7][C:6]([I:13])=[C:5]2[C:10]=1[CH2:2][NH:3][C:4]2=[O:14]

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 68492606HCID 68492606, compound

Product 1

HCID 68488661HCID 68488661, compoundYield 85%

Reagents, catalysts & solvents 1

HCID 6375NitromethaneSolvent

Procedure

In a similar manner to Step 4 of Example 16, 3-hydroxy-4-chloro-5-fluoro-7-iodo-2(1-methyl-1-phenylethyl)isoindolinone (806 mg, 1.81 mmol) was dissolved in nitromethane (32 mL), and the solution was treated with trifluoroacetic acid (1.40 mL, 18.1 mmol) and triethylsilane (0.578 mL, 3.62 mmol), followed by purification by slurry using diisopropylether to obtain 4-chloro-5-fluoro-7-iodoisoindolinone (477 mg, yield 85%).

Workup

  1. customfollowed by purification by slurry

Sources & evidence

ORD record
ord-5350404a6fff4ba0bf9473457275ea77
Source dataset
uspto-grants-2010_06
Patent number
US07745641B2

Reaction notes

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