Acetyl chloride → HCID 117667258, compound

HRID 712721Notes

Reaction equation

HRID 712721 reaction equation
Cl.[Br:2][C:3]1[CH:4]=[N:5][CH:6]=[C:7]([O:9][C@@H:10]2[CH2:15][CH2:14][CH2:13][NH:12][CH2:11]2)[CH:8]=1.[C:16](Cl)(=[O:18])[CH3:17].C(N(CC)C(C)C)(C)C>CN(C=O)C>[Br:2][C:3]1[CH:8]=[C:7]([O:9][C@@H:10]2[CH2:15][CH2:14][CH2:13][N:12]([C:16](=[O:18])[CH3:17])[CH2:11]2)[CH:6]=[N:5][CH:4]=1

Participants

5

Reactant 3

HCID 6367Acetyl chlorideHCID 81531DiisopropylethylamineHCID 117667564HCID 117667564, compound

Product 1

HCID 117667258HCID 117667258, compoundYield 50.3%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 3-bromo-5-((R)-piperidin-3-yloxy)-pyridine hydrochloride salt (525 mg, 1.8 mmol) in DMF (10 mL) is added acetyl chloride (0.19 mL, 2.7 mmol) and N,N-diisopropylethylamine (1.4 mL, 8.0 mmol). The mixture is stirred at room temperature for 16 h. The reaction is partitioned between H2O and EtOAc and the layers are separated. The aqueous is extracted with EtOAc and the combined organic layers are dried and concentrated. The crude product is purified by flash column chromatography to provide 271 mg of 1-[(R)-3-(5-bromo-pyridin-3-yloxy)-piperidin-1-yl]-ethanone.

Workup

  1. customThe reaction is partitioned between H2O and EtOAc
  2. customthe layers are separated
  3. extractionThe aqueous is extracted with EtOAc
  4. customthe combined organic layers are dried
  5. concentrationconcentrated
  6. customThe crude product is purified by flash column chromatography

Sources & evidence

ORD record
ord-5f1ee6166c274d3a90c7ff90473dadb9
Source dataset
uspto-grants-2015_11
Patent number
US09181272B2

Reaction notes

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