(Trifluoromethyl)trimethylsilane → HCID 67401736, compound

HRID 1186356

Reaction equation

HRID 1186356 reaction equation
[N:1]1([C:6]2[N:11]=[CH:10][C:9]([CH:12]=[O:13])=[CH:8][CH:7]=2)[CH2:5][CH2:4][CH2:3][CH2:2]1.[F:14][C:15]([Si](C)(C)C)([F:17])[F:16].[F-].C([N+](CCCC)(CCCC)CCCC)CCC>O1CCCC1>[N:1]1([C:6]2[CH:7]=[CH:8][C:9]([CH:12]([OH:13])[C:15]([F:17])([F:16])[F:14])=[CH:10][N:11]=2)[CH2:2][CH2:3][CH2:4][CH2:5]1

Participants

5

Reactant 3

HCID 552549(Trifluoromethyl)trimethylsilaneHCID 2724141Tetrabutylammonium FluorideHCID 27947756-(Pyrrolidin-1-yl)pyridine-3-carbaldehyde

Product 1

HCID 67401736HCID 67401736, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent2×

Procedure

According to Reference Example 8-12, by use of 6-(pyrrolidin-1-yl)-3-pyridinecarboxaldehyde (173 mg, 0.982 mmol), (trifluoromethyl)trimethylsilane (174 μL, 1.18 mmol), tetrabutylammonium fluoride (a 1.0 mol/L solution in tetrahydrofuran, 98.0 μL, 0.098 mmol) and tetrahydrofuran (5.0 mL), the mixture was stirred and reacted at room temperature for 30 minutes. Then, slurry purification was performed using hexane, to give 2-(pyrrolidin-1-yl)-5-(2,2,2-trifluoro-1-hydroxyethyl)-pyridine (Compound DH) (227 mg, yield: 94%).

Workup

  1. customreacted at room temperature for 30 minutes
  2. customThen, slurry purification

Sources & evidence

ORD record
ord-fd9eef4168e448158e86ec565aff527f
Source dataset
uspto-grants-2014_03
Patent number
US08673908B2

Linked notes

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