p-Anisoyl chloride → HCID 90102824, compound

HRID 1052569Notes

Reaction equation

HRID 1052569 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:8])[CH:5]=[N:6][CH:7]=1.C(N(C(C)C)CC)(C)C.[CH3:18][O:19][C:20]1[CH:28]=[CH:27][C:23]([C:24](Cl)=[O:25])=[CH:22][CH:21]=1>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:24](=[O:25])[C:23]2[CH:27]=[CH:28][C:20]([O:19][CH3:18])=[CH:21][CH:22]=2)[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 7477p-Anisoyl chlorideHCID 81531DiisopropylethylamineHCID 8176813-Amino-5-bromopyridine

Product 1

HCID 90102824HCID 90102824, compoundYield 99.7%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

5-Bromopyridin-3-amine (1.2 g, 6.94 mmol) was dissolved in dichloromethane (30 ml). Diisopropylethylamine (1.45 ml, 8.32 mmol) first and then a solution of 4-methoxybenzoyl chloride (1.18 g, 6.92 mmol) in dichloromethane (20 ml) were added. After stirring 1 h at room temperature the reaction mixture was diluted with ethyl acetate and washed with water and brine, dried over sodium sulphate, filtered and evaporated under reduced pressure to give 2.12 g (80% yield) of the title compound. Purity 78%.

Workup

  1. washwashed with water and brine
  2. dry with materialdried over sodium sulphate
  3. filtrationfiltered
  4. customevaporated under reduced pressure

Sources & evidence

ORD record
ord-fbc0ea2256784f078181b2e35e429be0
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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