Nitrogen → 4-(6-Bromo-2-pyridinyl)-1-methyl-4-piperidinol

HRID 460220Notes

Reaction equation

HRID 460220 reaction equation
[Li]CCCC.N#N.Br[C:9]1[CH:14]=[CH:13][CH:12]=[C:11]([Br:15])[N:10]=1.CC1C[CH2:21][NH:20][C:19](=O)[CH2:18]1.[CH2:24]1C[O:27][CH2:26][CH2:25]1>>[Br:15][C:11]1[N:10]=[C:9]([C:26]2([OH:27])[CH2:25][CH2:24][N:20]([CH3:21])[CH2:19][CH2:18]2)[CH:14]=[CH:13][CH:12]=1

Participants

6

Reactant 5

HCID 947NitrogenHCID 8028Tetrahydrofuran2×HCID 122742,6-DibromopyridineHCID 141468784-Methylpiperidin-2-oneHCID 178418339Butyllithium

Product 1

HCID 187720024-(6-Bromo-2-pyridinyl)-1-methyl-4-piperidinol

Conditions

Temperature
-70 °C

Procedure

To a solution of 1.07 M n-BuLi (36.4 mL) and dry THF (200 mL) chilled to −70° C. under a blanket of N2 was added 2,6-dibromopyridine (10 g, 38.9 mmol) in 50 mL of dry THF slowly to maintain a temperature less than −69° C. Stirred at −70° C. for 20 min. Added 4-methylpiperidone (4.8 mL, 38.9 mmol) and stirred the mixture at −70° C. for 1 h. Quenched with saturated NaHCO3 and extracted with EtOAc. Washed the organic layer with brine, dried (MgSO4) and concentrated in vacuo to give 6-bromo-1′-methyl-2′,3′,5′,6′-tetrahydro-1′H-[2,4′]bipyridinyl-4′-ol as a light-yellow solid. MS m/z: 272.3 (M+H). Calc'd for C11H15BrN2O-271.15.

Workup

  1. temperatureto maintain a temperature less than −69° C
  2. customQuenched with saturated NaHCO3
  3. extractionextracted with EtOAc
  4. washWashed the organic layer with brine
  5. dry with materialdried (MgSO4)
  6. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-c94f245718a04a41b75b157dc32d6bc1
Source dataset
uspto-grants-2007_03
Patent number
US07196104B2

Reaction notes

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