Ammonium Chloride → HCID 58360364, compound

HRID 407180Notes

Reaction equation

HRID 407180 reaction equation
Br[C:2]1[CH:7]=[CH:6][C:5]([Br:8])=[CH:4][N:3]=1.C([Li])CCC.[CH:14]([C:16]1[CH:17]=[C:18]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:19](=[O:26])[N:20]2[C:25]=1[CH:24]=[CH:23][CH:22]=[CH:21]2)=[O:15].[Cl-].[NH4+]>C1(C)C=CC=CC=1.ClCCl>[Br:8][C:5]1[CH:6]=[CH:7][C:2]([CH:14]([OH:15])[C:16]2[CH:17]=[C:18]([C:27]([O:29][CH2:30][CH3:31])=[O:28])[C:19](=[O:26])[N:20]3[C:25]=2[CH:24]=[CH:23][CH:22]=[CH:21]3)=[N:3][CH:4]=1

Participants

7

Reactant 4

HCID 25517Ammonium ChlorideHCID 693532,5-DibromopyridineHCID 20634151Ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylateHCID 178418339Butyllithium

Product 1

HCID 58360364HCID 58360364, compound

Reagents, catalysts & solvents 2

HCID 1140TolueneSolventHCID 6344DichloromethaneSolvent

Procedure

To a solution of 2,5-dibromopyridine (2.00 g, 8.44 mmol) in 50 mL of toluene at −78° C. was added n-butyllithium (2.5 M in toluene, 4.05 mL, 10.1 mmol) dropwise. After 2 h, a solution of ethyl 1-formyl-4-oxo-4H-quinolizine-3-carboxylate (1.86 g, 7.60 mmoL) in 50 mL of dichloromethane was added dropwise. The mixture was warmed to rt, and after 1 h, treated with saturated aqueous ammonium chloride and concentrated in vacuo. The residue was redissolved in dichloromethane, washed with brine, dried over sodium sulfate, filtered, and concentrated in vacuo. The residue was purified via silica gel chromatography, eluting with 30-100% ethyl acetate in hexanes to provide ethyl 1-[(5-bromopyridin-2-yl)(hydroxyl)methyl]-4-oxo-4H-quinolizine-3-carboxylate that gave a mass ion (ES+) of 404.7 (81Br) for [M+H]+.

Workup

  1. waitafter 1 h
  2. concentrationconcentrated in vacuo
  3. dissolutionThe residue was redissolved in dichloromethane
  4. washwashed with brine
  5. dry with materialdried over sodium sulfate
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified via silica gel chromatography
  9. washeluting with 30-100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-892b29df34474d92aa0c3e7d6a238bcd
Source dataset
uspto-grants-2014_06
Patent number
US08754220B2

Reaction notes

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