m-Anisoyl chloride → HCID 90102438, compound

HRID 1052577Notes

Reaction equation

HRID 1052577 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:21]=[C:22]([CH:26]=[CH:27][CH:28]=1)[C:23](Cl)=[O:24]>ClCCl.C(OCC)(=O)C>[Br:1][C:2]1[CH:3]=[C:4]([NH:8][C:23](=[O:24])[C:22]2[CH:26]=[CH:27][CH:28]=[C:20]([O:19][CH3:18])[CH:21]=2)[CH:5]=[N:6][CH:7]=1

Participants

6

Reactant 3

HCID 74374m-Anisoyl chlorideHCID 81531DiisopropylethylamineHCID 8176813-Amino-5-bromopyridine

Product 1

HCID 90102438HCID 90102438, compoundYield 115.4%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

5-Bromopyridin-3-amine (1.5 g, 8.67 mmol) was dissolved in dichloromethane (40 ml). Diisopropylethylamine (1.81 ml, 10.39 mmol) first and then a solution of 3-methoxybenzoyl chloride (1.18 ml, 8.66 mmol) in dichloromethane (25 ml) were added. After 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 3.07 g (89% yield) of the title compound. Purity 77%.

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-ba2620e69e254cd5b3bce9a5b9d7f98e
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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