Lithium Bromide → N-(3-Bromopropyl)-2-pyridinecarboxamide

HRID 2192392Notes

Reaction equation

HRID 2192392 reaction equation
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[C:7]([NH:9][CH2:10][CH2:11][CH2:12]OS(C)(=O)=O)=[O:8].[Br-:18].[Li+]>CC(C)=O>[Br:18][CH2:12][CH2:11][CH2:10][NH:9][C:7]([C:2]1[CH:3]=[CH:4][CH:5]=[CH:6][N:1]=1)=[O:8]

Participants

4

Reactant 2

HCID 82050Lithium BromideHCID 58348409HCID 58348409, compound

Product 1

HCID 12983474N-(3-Bromopropyl)-2-pyridinecarboxamideYield 81.3%

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent

Procedure

A mixture of methanesulfonic acid 3-[(pyridine-2-carbonyl)-amino]-propyl ester (Example 57a) (1.96 g) and lithium bromide (3.29 g) in acetone (19 mL) was heated to reflux for 2 h. The reaction mixture was cooled to room temperature, concentrated in vacuo and the residue partitioned between EtOAc/H2O (60 mL, 1:1). The phases were separated and the aqueous phase further extracted with EtOAc (2×25 mL). The combined organics were dried (MgSO4) and concentrated in vacuo to a brown oil which solidified on standing. Purification by silica gel chromatography eluting with 0-100% EtOAc/cyclohexane gives the sub-titled compound (1.5 g) as a white solid.

Workup

  1. temperaturewas heated
  2. temperatureto reflux for 2 h
  3. concentrationconcentrated in vacuo
  4. customthe residue partitioned between EtOAc/H2O (60 mL, 1:1)
  5. customThe phases were separated
  6. extractionthe aqueous phase further extracted with EtOAc (2×25 mL)
  7. dry with materialThe combined organics were dried (MgSO4)
  8. concentrationconcentrated in vacuo to a brown oil which
  9. customPurification by silica gel chromatography
  10. washeluting with 0-100% EtOAc/cyclohexane

Sources & evidence

ORD record
ord-b65cbff9c3714ae7ab05bda0f0b01ea8
Source dataset
uspto-grants-2012_12
Patent number
US08329729B2

Reaction notes

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