HCID 86699397, compound → HCID 67974538, compound

HRID 1777685Notes

Reaction equation

HRID 1777685 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[NH:7][C:6]([Si](CC)(CC)CC)=[C:5]2[CH2:19][CH2:20][NH:21][C:22](=[O:37])[C:23]1[CH:28]=[CH:27][C:26]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=2)=[CH:25][CH:24]=1>FC(F)(F)C(O)=O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[C:9]([F:11])[CH:10]=1)[NH:7][CH:6]=[C:5]2[CH2:19][CH2:20][NH:21][C:22](=[O:37])[C:23]1[CH:24]=[CH:25][C:26]([CH2:29][C:30]2[CH:35]=[CH:34][CH:33]=[C:32]([F:36])[CH:31]=2)=[CH:27][CH:28]=1

Participants

3

Reactant 1

HCID 86699397HCID 86699397, compound

Product 1

HCID 67974538HCID 67974538, compoundYield 19%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N-(2-(5-Chloro-7-fluoro-2-(triethylsilyl)-1H-indol-3-yl)ethyl)-4-(3-fluorobenzyl)benzamide (0.102 g; 0.189 mmol) was dissolved in trifluoroacetic acid (3 mL) and stirred at room temperature for 3 hours. The solution was concentrated under reduced pressure and the crude material was purified by flash chromatography on silica gel (eluent 20 to 100% ethyl acetate in heptane) to afford 0.015 g (19%) of the title compound as a white solid.

Workup

  1. concentrationThe solution was concentrated under reduced pressure
  2. customthe crude material was purified by flash chromatography on silica gel (eluent 20 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-174f1bca7ac742509a58ff0344a8fd7f
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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