Tetrabutylammonium Fluoride → HCID 53465552, compound

HRID 2280254Notes

Reaction equation

HRID 2280254 reaction equation
CS(O[CH2:6][CH2:7][N:8]1[CH:12]=[C:11]([C:13]2[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=2)[C:10]([C:19]2[CH:24]=[CH:23][C:22]([O:25][CH2:26][C:27]3[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=3)=[CH:21][CH:20]=2)=[N:9]1)(=O)=O.[F-:33].C([N+](CCCC)(CCCC)CCCC)CCC>C1COCC1>[CH2:26]([O:25][C:22]1[CH:23]=[CH:24][C:19]([C:10]2[C:11]([C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[CH:12][N:8]([CH2:7][CH2:6][F:33])[N:9]=2)=[CH:20][CH:21]=1)[C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1

Participants

4

Reactant 2

HCID 2724141Tetrabutylammonium FluorideHCID 86706032HCID 86706032, compound

Product 1

HCID 53465552HCID 53465552, compoundYield 23%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Intermediate 3A, 2-(3-(4-(benzyloxy)phenyl)-4-(pyridin-4-yl)-1H-pyrazol-1-yl)ethyl methanesulfonate (11 g) was added to a 1M solution of tetrabutylammonium fluoride in THF (150 mL) and the reaction mixture was stirred overnight at ambient temperature. The reaction mixture was concentrated under reduced pressure and the residue was purified by flash column chromatography to obtain the desired Intermediate 3B, 4-(3-(4-(benzyloxy)phenyl)-1-(2-fluoroethyl)-1H-pyrazol-4-yl)pyridine (2.1 g, 23%) and the side product 4-(3-(4-(benzyloxy)phenyl)-1-vinyl-1H-pyrazol-4-yl)pyridine (2.0 g, 30%).

Workup

  1. concentrationThe reaction mixture was concentrated under reduced pressure
  2. customthe residue was purified by flash column chromatography

Sources & evidence

ORD record
ord-db428dcc15c04db8a3d69a40c93bb422
Source dataset
uspto-grants-2015_09
Patent number
US09138494B2

Reaction notes

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