Potassium Phosphate, Tribasic → 2-Fluoro-3-(tetrahydro-2H-pyran-4-yl)pyridine

HRID 1846750Notes

Reaction equation

HRID 1846750 reaction equation
Br[C:2]1[C:3]([F:8])=[N:4][CH:5]=[CH:6][CH:7]=1.CC1(C)C(C)(C)OC([C:17]2[CH2:18][CH2:19][O:20][CH2:21][CH:22]=2)O1.[O-]P([O-])([O-])=O.[K+].[K+].[K+]>O1CCOCC1.O>[F:8][C:3]1[C:2]([CH:17]2[CH2:22][CH2:21][O:20][CH2:19][CH2:18]2)=[CH:7][CH:6]=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 62657Potassium Phosphate, TribasicHCID 27627783-Bromo-2-fluoropyridineHCID 66634485HCID 66634485, compound

Product 1

HCID 593271552-Fluoro-3-(tetrahydro-2H-pyran-4-yl)pyridineYield 51.2%

Reagents, catalysts & solvents 1

HCID 218864351,4-Dioxane--water (1/1)Solvent

Procedure

A mixture of 3-bromo-2-fluoro-pyridine (500 mg, 2.84 mmol), 4-(4,4,5,5-Tetramethyl-[1,3]dioxolan-2-yl)-3,6-dihydro-2H-pyran (656 mg, 3.12 mmol), K3PO4 (1.2 g, 5.68 mmol), and Pd (dppf)Cl2 (208 mg, 0.284 mmol) in 1,4-Dioxane/H2O (5:1) (30 mL) was heated to reflux overnight under N2 atmosphere. The reaction mixture was filtered and the filtrate was concentrated and purification by prep-TLC to give 2-fluoro-3-(tetrahydro-pyran-4-yl)-pyridine (260 mg, 1.45 mmol, 51.2%).

Workup

  1. temperaturewas heated
  2. temperatureto reflux overnight under N2 atmosphere
  3. filtrationThe reaction mixture was filtered
  4. concentrationthe filtrate was concentrated
  5. custompurification by prep-TLC

Sources & evidence

ORD record
ord-cc8b11415ef5485b8828e6af21e6b954
Source dataset
uspto-grants-2015_02
Patent number
US08952037B2

Reaction notes

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