Cesium carbonate → 3-[[3,5,6-Trifluoro-4-[(2,2-dimethyldioxolan-4-yl)methoxy]pyridin-2-yl]oxy]-4-(benzyloxy)benzonitrile

HRID 1267090Notes

Reaction equation

HRID 1267090 reaction equation
F[C:2]1[C:7]([F:8])=[C:6]([O:9][CH2:10][CH:11]2[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12]2)[C:5]([F:18])=[C:4]([F:19])[N:3]=1.C([O-])([O-])=O.[Cs+].[Cs+].[OH:26][C:27]1[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=1[O:35][CH2:36][C:37]1[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=1)[C:30]#[N:31]>CC#N>[F:8][C:7]1[C:2]([O:26][C:27]2[CH:28]=[C:29]([CH:32]=[CH:33][C:34]=2[O:35][CH2:36][C:37]2[CH:42]=[CH:41][CH:40]=[CH:39][CH:38]=2)[C:30]#[N:31])=[N:3][C:4]([F:19])=[C:5]([F:18])[C:6]=1[O:9][CH2:10][CH:11]1[CH2:15][O:14][C:13]([CH3:17])([CH3:16])[O:12]1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 154534514-(Benzyloxy)-3-hydroxybenzonitrileHCID 234422212,3,5,6-Tetrafluoro-4-[(2,2-dimethyldioxolan-4-yl)methoxy]pyridine

Product 1

HCID 695506003-[[3,5,6-Trifluoro-4-[(2,2-dimethyldioxolan-4-yl)methoxy]pyridin-2-yl]oxy]-4-(benzyloxy)benzonitrileYield 56.1%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 2,3,5,6-tetrafluoro-4-[(2,2-dimethyidioxolan-4-yl)methoxy]pyridine (3.2 g, 11 mmol) in CH3CN (20 mL) was added Cs2CO3 (3.8 g, 12 mmol) and 3-hydroxy-4-(benzyloxy)benzonitrile (2.5 g, 11 mmol). After stirring for 24 hours the reaction was partitioned with water and ethyl acetate. The layers were separated, washed with water and brine, dried (Na2SO4), and the solvent was removed in vacuo. The residue was triturated with hexane/ethyl acetate (1/1) and the resulting solid was collected by filtration to give 3-[[3,5,6-trifluoro-4-[(2,2-dimethyldioxolan-4-yl)methoxy]pyridin-2-yl]oxy]-4-(benzyloxy)benzonitrile (3.0 g).

Workup

  1. customwas partitioned with water and ethyl acetate
  2. customThe layers were separated
  3. washwashed with water and brine
  4. dry with materialdried (Na2SO4)
  5. customthe solvent was removed in vacuo
  6. customThe residue was triturated with hexane/ethyl acetate (1/1)
  7. filtrationthe resulting solid was collected by filtration

Sources & evidence

ORD record
ord-08dd5f32aeb5401d8c1c78a7a8fcaec3
Source dataset
uspto-grants-2003_04
Patent number
US06552030B2

Reaction notes

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