Water → 2-Bromo-6-(2,2-difluoro-cyclopropylmethoxy)-pyridine

HRID 40511

Reaction equation

HRID 40511 reaction equation
[F:1][C:2]1([F:7])[CH2:4][CH:3]1[CH2:5][OH:6].[H-].[Na+].[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13](F)[N:12]=1.O>O1CCOCC1.CN(C=O)C>[Br:10][C:11]1[CH:16]=[CH:15][CH:14]=[C:13]([O:6][CH2:5][CH:3]2[CH2:4][C:2]2([F:7])[F:1])[N:12]=1

Participants

7

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 6394382-Bromo-6-fluoropyridineHCID 2761401(2,2-Difluorocyclopropyl)methanol

Product 1

HCID 866890142-Bromo-6-(2,2-difluoro-cyclopropylmethoxy)-pyridine

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

To 307 mg (2.84 mmol) (2,2-difluorocyclopropyl)methanol in 1,4-dioxane (10 mL) is added 69 mg (2.84 mmol) sodium hydride and 500 mg (2.84 mmol) 2-bromo-6-fluoropyridine. The mixture is stirred for 2 h at 90° C. Water and DMF are added and the mixture is filtered and concentrated in vacuo. The residue is purified by HPLC (C18 RP Sunfire, acetonitrile/water (+0.1% TFA)) to yield the desired product.

Workup

  1. filtrationthe mixture is filtered
  2. concentrationconcentrated in vacuo
  3. customThe residue is purified by HPLC (C18 RP Sunfire, acetonitrile/water (+0.1% TFA))

Sources & evidence

ORD record
ord-8d611a51858c41169343e7666344cf94
Source dataset
uspto-grants-2013_09
Patent number
US08530461B2

Linked notes

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