HCID 86699395, compound → HCID 67974647, compound

HRID 1777683Notes

Reaction equation

HRID 1777683 reaction equation
[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][C:8]([Si](CC)(CC)CC)=[C:7]2[CH2:20][CH2:21][NH:22][C:23](=[O:38])[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=2)=[CH:26][CH:25]=1)(=[O:3])[CH3:2]>FC(F)(F)C(O)=O>[C:1]([C:4]1[CH:5]=[C:6]2[C:10](=[CH:11][CH:12]=1)[NH:9][CH:8]=[C:7]2[CH2:20][CH2:21][NH:22][C:23](=[O:38])[C:24]1[CH:29]=[CH:28][C:27]([CH2:30][C:31]2[CH:36]=[CH:35][CH:34]=[C:33]([F:37])[CH:32]=2)=[CH:26][CH:25]=1)(=[O:3])[CH3:2]

Participants

3

Reactant 1

HCID 86699395HCID 86699395, compound

Product 1

HCID 67974647HCID 67974647, compoundYield 58%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N-(2-(5-Acetyl-2-(triethylsilyl)-1H-indol-3-yl)ethyl)-4-(3-fluorobenzyl)benzamide (0.043 g; 0.109 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 0.020 g (58%) of the title compound as a yellow foam.

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-4594990c79cc4f07a39dcaa530b27fc2
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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