N-(2-(5-cyano-2-(triethylsilyl)-1H-indol-3-yl)ethyl)-5-(2,5-difluorobenzyl)isoxazole-3-carboxamide → HCID 66831846, compound

HRID 58761Notes

Reaction equation

HRID 58761 reaction equation
[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([Si](CC)(CC)CC)=[C:6]2[CH2:19][CH2:20][NH:21][C:22]([C:24]1[CH:28]=[C:27]([CH2:29][C:30]2[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=2[F:37])[O:26][N:25]=1)=[O:23])#[N:2]>FC(F)(F)C(O)=O>[C:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][CH:7]=[C:6]2[CH2:19][CH2:20][NH:21][C:22]([C:24]1[CH:28]=[C:27]([CH2:29][C:30]2[CH:35]=[C:34]([F:36])[CH:33]=[CH:32][C:31]=2[F:37])[O:26][N:25]=1)=[O:23])#[N:2]

Participants

3

Reactant 1

HCID 66832142N-(2-(5-cyano-2-(triethylsilyl)-1H-indol-3-yl)ethyl)-5-(2,5-difluorobenzyl)isoxazole-3-carboxamide

Product 1

HCID 66831846HCID 66831846, compoundYield 47%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

N-(2-(5-cyano-2-(triethylsilyl)-1H-indol-3-yl)ethyl)-5-(2,5-difluorobenzyl)isoxazole-3-carboxamide (0.036 g; 0.069 mmol) was dissolved in trifluoroacetic acid (2 mL) and the resulting mixture was stirred at room temperature for 2 hours. The mixture was concentrated under reduced pressure with toluene. The crude mixture was purified flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.012 g (47%) of N-(2-(5-cyano-1H-indol-3-yl)ethyl)-5-(2,5-difluorobenzyl)isoxazole-3-carboxamide as a white solid.

Workup

  1. concentrationThe mixture was concentrated under reduced pressure with toluene
  2. customThe crude mixture was purified flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-a2de24e174a340909f627858f000a815
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

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