Water → HCID 66825621, compound

HRID 920317Notes

Reaction equation

HRID 920317 reaction equation
[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([CH2:13][C:14](OCC)=[O:15])=[N:11][CH:12]=2)=[CH:4][C:3]=1[C:21]([F:24])([F:23])[F:22].[BH4-].[Na+].O.C(Cl)Cl>C(O)C>[Cl:1][C:2]1[CH:20]=[CH:19][C:5]([O:6][C:7]2[CH:8]=[CH:9][C:10]([CH2:13][CH2:14][OH:15])=[N:11][CH:12]=2)=[CH:4][C:3]=1[C:21]([F:24])([F:22])[F:23]

Participants

6

Reactant 4

HCID 962WaterHCID 6344DichloromethaneHCID 4311764Sodium borohydrideHCID 71236655HCID 71236655, compound

Product 1

HCID 66825621HCID 66825621, compoundYield 35.4%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
20 °C

Procedure

To a solution of ethyl 2-(5-(4-chloro-3-(trifluoromethyl)phenoxy)pyridin-2-yl)acetate (2 g, 4.45 mmol) in ethanol (20 mL) was added sodium borohydride (1.683 g, 44.5 mmol). The reaction mixture was stirred at 20° C. for 10 hr. To the reaction mixture was added 50 mL of H2O and 50 mL of CH2Cl2. The organic layer was separated and dried over Na2SO4 and concentrated under reduced pressure. The crude product was added to a prep HPLC column eluting with MeCN/TFA 0.1% to provide 2-(5-(4-chloro-3-(trifluoromethyl)phenoxy)pyridin-2-yl)ethanol (500 mg, 25.5%).

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over Na2SO4
  3. concentrationconcentrated under reduced pressure
  4. additionThe crude product was added to a prep HPLC column
  5. washeluting with MeCN/TFA 0.1%

Sources & evidence

ORD record
ord-0c3200632afd4ffcb74e53fd10de8de0
Source dataset
uspto-grants-2016_03
Patent number
US09273054B2

Reaction notes

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