Potassium Carbonate → (2,6-Dichloro-5-fluoropyridin-3-yl)methanol

HRID 2066866Notes

Reaction equation

HRID 2066866 reaction equation
[Cl:1][C:2]1[N:10]=[C:9]([Cl:11])[C:8]([F:12])=[CH:7][C:3]=1[C:4](O)=[O:5].B.C1COCC1.C([O-])([O-])=O.[K+].[K+]>C1COCC1>[Cl:1][C:2]1[C:3]([CH2:4][OH:5])=[CH:7][C:8]([F:12])=[C:9]([Cl:11])[N:10]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 2723981Borane;tetrahydrofuranHCID 27336592,6-Dichloro-5-fluoronicotinic acid

Product 1

HCID 23114857(2,6-Dichloro-5-fluoropyridin-3-yl)methanolYield 55%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 2,6-dichloro-5-fluoro-nicotinic acid (1.11 g, 5.29 mmol) in 20 mL of THF at 0° C., was added BH3.THF (1M, 8 mL, 8 mmol) and the mixture was stirred at room temperature for 5 h. K2CO3 (4 g) was added and the mixture was stirred for 2 h, filtered and concentrated. The residue was purified by flash chromatography (eluent: 10 to 50% ethyl acetate+0.1% triethylamine in hexane) to afford 55a as a white solid (0.57 g, 55% yield).

Workup

  1. stirringthe mixture was stirred for 2 h
  2. filtrationfiltered
  3. concentrationconcentrated
  4. customThe residue was purified by flash chromatography (eluent: 10 to 50% ethyl acetate+0.1% triethylamine in hexane)

Sources & evidence

ORD record
ord-1aac1542970647e48536d93d93d1c104
Source dataset
uspto-grants-2012_10
Patent number
US08293729B2

Reaction notes

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