Trifluoroacetic acid → HCID 10202112, compound

HRID 857380Notes

Reaction equation

HRID 857380 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:17]3[C:16]([CH:18](O)[CH2:19][CH3:20])=[CH:15][C:14]([F:22])=[CH:13][C:12]=3[N:11]3[CH2:23][CH2:24][CH:25]([CH2:26][C:27]([OH:29])=[O:28])[C:10]=23)=[CH:4][CH:3]=1.FC(F)(F)C(O)=O.C([SiH](CC)CC)C>C(Cl)Cl>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([S:8][C:9]2[C:17]3[C:16]([CH2:18][CH2:19][CH3:20])=[CH:15][C:14]([F:22])=[CH:13][C:12]=3[N:11]3[CH2:23][CH2:24][CH:25]([CH2:26][C:27]([OH:29])=[O:28])[C:10]=23)=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 10224846HCID 10224846, compound

Product 1

HCID 10202112HCID 10202112, compoundYield 29.9%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of [9-[(4-chlorophenyl)thio]-6-fluoro-8-(1-hydroxypropyl)-2,3-dihydro-1H-pyrrolo[1,2-a]indol-1-yl]acetic acid (Example 19, 36 mg, 0.08 mmol) in CH2Cl2 were added trifluoroacetic acid (0.5 mL) and triethylsilane (0.2 mL). The mixture was stirred for 1 hour at r.t. and solvent was removed. The residue was purified by silica gel chromatography eluted with 40% EtOAc/hexane containing 1% of AcOH to give 10 mg the title compound as a white foam.

Workup

  1. customsolvent was removed
  2. customThe residue was purified by silica gel chromatography
  3. washeluted with 40% EtOAc/hexane containing 1% of AcOH

Sources & evidence

ORD record
ord-a55f13ff1dce450a9d3a85ae7058e996
Source dataset
uspto-grants-2006_12
Patent number
US07144913B2

Reaction notes

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