Acetonitrile → HCID 117667693, compound

HRID 712728Notes

Reaction equation

HRID 712728 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8](O)([CH3:10])[CH3:9])[CH:5]=[N:6][CH:7]=1.F[C:13](F)(F)[C:14]([OH:16])=O.C(#[N:21])C>>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([NH:21][C:14](=[O:16])[CH3:13])([CH3:10])[CH3:9])[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 3

HCID 6342AcetonitrileHCID 6422Trifluoroacetic acidHCID 223919662-(5-Bromo-3-pyridyl)propan-2-ol

Product 1

HCID 117667693HCID 117667693, compound

Procedure

To the mixture of 2-(5-bromo-pyridin-3-yl)-propan-2-ol (700 mg, 3.24 mmol) in acetonitrile (14 mL) is added dropwise boron trifluoride diethyl ether complex (1.1 mL, 8.7 mmol) at room temperature. Then trifluoroacetic acid (1.8 ml, 23 mmol) is added dropwise and the reaction mixture is heated to reflux for 16 hrs. All the solvent is removed in vacuo and DCM is added. 1.0 M Na2CO3 solution is used to adjust the pH of aqueous phase to 8. The aqueous layer is separated and extracted with DCM twice. All the organic layers are combined and concentrated to give the crude product. Purification by flash column chromatography affords 252 mg of N-[1(5-bromo-pyridin-3-yl)-1-methyl-ethyl]-acetamide.

Workup

  1. additionis added dropwise boron trifluoride diethyl ether complex (1.1 mL, 8.7 mmol) at room temperature
  2. temperaturethe reaction mixture is heated
  3. temperatureto reflux for 16 hrs
  4. customAll the solvent is removed in vacuo and DCM
  5. additionis added
  6. customThe aqueous layer is separated
  7. extractionextracted with DCM twice
  8. concentrationconcentrated
  9. customto give the crude product
  10. customPurification by flash column chromatography

Sources & evidence

ORD record
ord-f206c1456da142c28f2bcec00eb3a6b5
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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