Potassium Phosphate, Tribasic → 3-Cyclopropyl-2-fluoropyridine

HRID 2205280Notes

Reaction equation

HRID 2205280 reaction equation
[F:1][C:2]1[C:7](I)=[CH:6][CH:5]=[CH:4][N:3]=1.[CH:9]1([B-](F)(F)F)[CH2:11][CH2:10]1.[K+].C1(P(C2CCCCC2)C2CCCCC2)CCCCC1.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>C1(C)C=CC=CC=1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.O>[CH:9]1([C:7]2[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=2)[CH2:11][CH2:10]1

Participants

8

Reactant 4

HCID 62657Potassium Phosphate, TribasicHCID 75806TricyclohexylphosphineHCID 70095012-Fluoro-3-iodopyridineHCID 23697338Potassium cyclopropyltrifluoroborate

Product 1

HCID 593270243-Cyclopropyl-2-fluoropyridineYield 108.8%

Reagents, catalysts & solvents 3

HCID 167845palladium(II) acetateCatalystHCID 962WaterSolvent2×HCID 1140TolueneSolvent

Conditions

Temperature
130 °C

Procedure

2-Fluoro-3-iodopyridine (300 mg, 1.34 mmol), potassium cyclopropyltrifluoroborate (498 mg, 3.36 mmol), palladium (II) acetate (30 mg, 0.135 mmol) are dissolved in toluene (4 mL) under a nitrogen flow. Tricyclohexylphosphine (75 mg, 0.27 mmol), tri-potassium phosphate (1.1 g, 5.38 mmol) and water (0.4 mL) are added and the reaction mixture is heated under microwave irradation (130° C.) for 2 h. At rt, water is added and the aqueous layer is extracted with DCM. Then the organic layer is washed with water and brine, separated and dried to furnish 3-cyclopropyl-2-fluoro-pyridine (200 mg, 97%).

Workup

  1. extractionthe aqueous layer is extracted with DCM
  2. washThen the organic layer is washed with water and brine
  3. customseparated
  4. customdried

Sources & evidence

ORD record
ord-68608f14fab24efdb87e0f5c7f9c506d
Source dataset
uspto-grants-2016_06
Patent number
US09371282B2

Reaction notes

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