Ethyl Acetate → HCID 90102989, compound

HRID 1052635Notes

Reaction equation

HRID 1052635 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([NH2:9])[C:5]([Cl:8])=[N:6][CH:7]=1.C(N(C(C)C)CC)(C)C.CO[C:21]1[CH:22]=[C:23]([CH:27]=[CH:28][CH:29]=1)[C:24](Cl)=[O:25].[C:30](OCC)(=[O:32])C>ClCCl>[Br:1][C:2]1[CH:3]=[C:4]([NH:9][C:24](=[O:25])[C:23]2[CH:22]=[CH:21][C:29]([O:32][CH3:30])=[CH:28][CH:27]=2)[C:5]([Cl:8])=[N:6][CH:7]=1

Participants

6

Reactant 4

HCID 8857Ethyl AcetateHCID 74374m-Anisoyl chlorideHCID 81531DiisopropylethylamineHCID 218583543-Amino-5-bromo-2-chloropyridine

Product 1

HCID 90102989HCID 90102989, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

5-Bromo-2-chloropyridin-3-amine (1.5 g, 7.23 mmol) was dissolved in dichloromethane (30 ml). Diisopropylethylamine (1.52 ml, 8.67 mmol) first and then a solution of 3-methoxybenzoyl chloride (1.08 ml, 7.95 mmol) in dichloromethane (20 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 2.8 g (92% yield) of the title compound. Purity 81%.

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-4eefbe75c9d84c55846ee30d9c176e99
Source dataset
uspto-grants-2016_07
Patent number
US09388189B2

Reaction notes

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