Acetyl chloride → HCID 68938130, compound

HRID 1878621Notes

Reaction equation

HRID 1878621 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH2:9][CH2:10][NH:11][CH2:12][CH:13]=2)[CH:5]=[N:6][CH:7]=1.[C:14](Cl)(=[O:16])[CH3:15]>C(Cl)Cl>[Br:1][C:2]1[CH:3]=[C:4]([C:8]2[CH2:9][CH2:10][N:11]([C:14](=[O:16])[CH3:15])[CH2:12][CH:13]=2)[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 6367Acetyl chloride2×HCID 68932809HCID 68932809, compound2×

Product 1

HCID 68938130HCID 68938130, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

To a solution of 5-bromo-1′,2′,3′,6′-tetrahydro-[3,4′]bipyridinyl (Intermediate 214) (1 eq, 0.523 mmol, 125 mg) in DCM (5 ml) at 0° C. is added TEA (1.1 eq, 0.575 mmol, 0.08 ml). Then acetyl chloride (1.1 eq, 0.575 mmol, 0.041 ml) is added and the resulting mixture is stirred for 20 h at r.t. Additional TEA (1.1 eq, 0.575 mmol, 0.08 ml) and acetyl chloride (1.1 eq, 0.575 mmol, 0.041 ml) are added and stirring is continued for another 1.5 h. The mixture is diluted with DCM and washed with 10% aqueous K2CO3 solution. The organic layer is dried over MgSO4, filtered, and the solvent is removed under reduced pressure giving the title compound; [M+H]+=281/283.

Workup

  1. stirringstirring
  2. waitis continued for another 1.5 h
  3. washwashed with 10% aqueous K2CO3 solution
  4. dry with materialThe organic layer is dried over MgSO4
  5. filtrationfiltered
  6. customthe solvent is removed under reduced pressure

Sources & evidence

ORD record
ord-e170d263582b4ea1b53669cc610153a1
Source dataset
uspto-grants-2012_11
Patent number
US08314112B2

Reaction notes

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