HCID 86699396, compound → HCID 67974414, compound

HRID 1777684Notes

Reaction equation

HRID 1777684 reaction equation
[F:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][CH:38]=1)[CH2:5][C:6]1[CH:35]=[CH:34][C:9]([C:10]([NH:12][CH2:13][CH2:14][C:15]2[C:23]3[C:18](=[CH:19][C:20]([F:26])=[C:21]([F:25])[C:22]=3[F:24])[NH:17][C:16]=2[Si](CC)(CC)CC)=[O:11])=[CH:8][CH:7]=1>FC(F)(F)C(O)=O>[F:1][C:2]1[CH:3]=[C:4]([CH:36]=[CH:37][CH:38]=1)[CH2:5][C:6]1[CH:35]=[CH:34][C:9]([C:10]([NH:12][CH2:13][CH2:14][C:15]2[C:23]3[C:18](=[CH:19][C:20]([F:26])=[C:21]([F:25])[C:22]=3[F:24])[NH:17][CH:16]=2)=[O:11])=[CH:8][CH:7]=1

Participants

3

Reactant 1

HCID 86699396HCID 86699396, compound

Product 1

HCID 67974414HCID 67974414, compoundYield 60.3%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4-(3-Fluorobenzyl)-N-(2-(4,5,6-trifluoro-2-(triethylsilyl)-1H-indol-3-yl)ethyl)benzamide (0.057 g; 0.105 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 0.027 g (60%) 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-38c028327fa2471e96b4f7bc9b01b042
Source dataset
uspto-grants-2016_02
Patent number
US09266832B2

Reaction notes

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