Water → (2-Fluoro-5-(2-fluoropyridin-3-yl)phenyl)methanol

HRID 335947Notes

Reaction equation

HRID 335947 reaction equation
[F:1][C:2]1[C:7](B(O)O)=[CH:6][CH:5]=[CH:4][N:3]=1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O.C([O:23][CH2:24][CH3:25])(=O)C>O1CCOCC1.C(C1C(C(C)(C)C)=C([Pd]Cl)C=CC=1NC)(C)(C)C>[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:7]2[C:2]([F:1])=[N:3][CH:4]=[CH:5][CH:6]=2)=[CH:4][C:25]=1[CH2:24][OH:23]

Participants

7

Reactant 4

HCID 962Water2×HCID 8857Ethyl AcetateHCID 62657Potassium Phosphate, TribasicHCID 27832702-Fluoropyridine-3-boronic acid

Product 1

HCID 67383551(2-Fluoro-5-(2-fluoropyridin-3-yl)phenyl)methanolYield 47%

Reagents, catalysts & solvents 2

HCID 178482226HCID 178482226, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

The crude oil was dissolved in dioxane (100 mL) and treated with 2-fluoropyridin-3-ylboronic acid (3.47 g, 24.63 mmol), potassium phosphate (5.23 g, 24.63 mmol), and 1,1-bis[(di-t-butyl-p-methylaminophenyl]palladium(II) chloride (0.25 g, 0.35 mmol). Water (10 mL) was added and the reaction heated to 90° C. for 10 min. Water (300 mL) and ethyl acetate (200 mL) were added and the phases mixed and separated. The organic was dried with magnesium sulfate and evaporated to dryness under reduced pressure. Purification of the crude material using silica chromatography (hexane to ethyl acetate gradient) gave (2-fluoro-5-(2-fluoropyridin-3-yl)phenyl)methanol (2.54 g, 47%). MS m/z=222.1 [M+H]+. Calculated for C12H9F2NO: 221.05.

Workup

  1. additionthe phases mixed
  2. customseparated
  3. dry with materialThe organic was dried with magnesium sulfate
  4. customevaporated to dryness under reduced pressure
  5. customPurification of the crude material

Sources & evidence

ORD record
ord-331e95fa45b44304864b3343cdd4825d
Source dataset
uspto-grants-2014_11
Patent number
US08883782B2

Reaction notes

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