Triethylsilane → HCID 117988564, compound

HRID 2206110Notes

Reaction equation

HRID 2206110 reaction equation
[CH3:1][O:2][C:3]1[C:8]2[N:9](COCC[Si](C)(C)C)[CH:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[C:7]=2[C:6]([C:27]#[N:28])=[CH:5][N:4]=1.C([SiH](CC)CC)C>FC(F)(F)C(O)=O>[CH3:1][O:2][C:3]1[C:8]2[NH:9][CH:10]=[C:11]([C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][C:13]=3[CH3:18])[C:7]=2[C:6]([C:27]#[N:28])=[CH:5][N:4]=1

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 131735834HCID 131735834, compound

Product 1

HCID 117988564HCID 117988564, compoundYield 149.5%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of 7-methoxy-3-(2-methylphenyl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-c]pyridine-4-carbonitrile (1.20 g) in trifluoroacetic acid (15.25 mL) was added triethylsilane (1.46 mL) at room temperature, and the mixture was stirred at room temperature for 3 hr. The reaction mixture was concentrated under reduced pressure, and the obtained residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/hexane), and crystallized from ethyl acetate and hexane to give the title compound (1.20 g).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe obtained residue was purified by silica gel column chromatography (basic silica gel, ethyl acetate/hexane)
  3. customcrystallized from ethyl acetate and hexane

Sources & evidence

ORD record
ord-538908279a0b4acf9f30bd59ef9df697
Source dataset
uspto-grants-2016_06
Patent number
US09371320B2

Reaction notes

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