Triethylsilane → (4-{4,9-Bis[(difluoromethyl)oxy]-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl}-3-fluorophenyl)acetic acid

HRID 222428Notes

Reaction equation

HRID 222428 reaction equation
[F:1][CH:2]([F:34])[O:3][C:4]1[C:12]2[C:11](=O)[N:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][C:15]=3[F:24])[CH:9]([OH:25])[C:8]=2[C:7]([O:26][CH:27]([F:29])[F:28])=[C:6]2[CH:30]=[CH:31][CH:32]=[CH:33][C:5]=12.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[F:34][CH:2]([F:1])[O:3][C:4]1[C:12]2[CH2:11][N:10]([C:14]3[CH:19]=[CH:18][C:17]([CH2:20][C:21]([OH:23])=[O:22])=[CH:16][C:15]=3[F:24])[C:9](=[O:25])[C:8]=2[C:7]([O:26][CH:27]([F:28])[F:29])=[C:6]2[CH:30]=[CH:31][CH:32]=[CH:33][C:5]=12

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 58231497HCID 58231497, compound

Product 1

HCID 24738236(4-{4,9-Bis[(difluoromethyl)oxy]-1-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl}-3-fluorophenyl)acetic acidYield 45.8%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of (4-{4,9-bis[(difluoromethyl)oxy]-1-hydroxy-3-oxo-1,3-dihydro-2H-benzo[f]isoindol-2-yl}-3-fluorophenyl)acetic acid (0.035 g, 0.072 mmol) in trifluoroacetic acid (2 ml) cooled to 0° C., was added triethylsilane (0.019 ml, 0.110 mmol). Stirring continued at 0° C. for 5 minutes and then the mixture was evaporated. The crude mixture was purified using MDAP. The clean fractions were evaporated to give the title compound (0.015 g, 0.033 mmol). LC/MS: Rt=3.15, [MH]+ 468.

Workup

  1. customthe mixture was evaporated
  2. customThe crude mixture was purified
  3. customThe clean fractions were evaporated

Sources & evidence

ORD record
ord-20049876481a482c873e583c4875ef5a
Source dataset
uspto-grants-2012_06
Patent number
US08207213B2

Reaction notes

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