Pyridine → HCID 68291492, compound

HRID 2174548Notes

Reaction equation

HRID 2174548 reaction equation
[NH2:1][C:2]1[CH:11]=[C:10]([Cl:12])[C:9]([I:13])=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].N1C=CC=CC=1.Cl[C:21](=[O:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24]>ClCCl>[Cl:12][C:10]1[C:9]([I:13])=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]([NH:1][C:21](=[O:28])[CH2:22][C:23]([O:25][CH2:26][CH3:27])=[O:24])[CH:11]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 118931Ethyl 3-chloro-3-oxopropionateHCID 10852539Methyl 2-amino-4-chloro-5-iodobenzoate2×

Product 1

HCID 68291492HCID 68291492, compoundYield 75.3%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a solution of methyl 2-amino-4-chloro-5-iodobenzoate (Intermediate 2) (8 g, 25.7 mmol) and pyridine (2.18 mL, 27 mmol) in dichloromethane (200 mL) was added ethyl 3-chloro-3-oxopropanoate (Aldrich, 3.45 mL, 27 mmol) and the reaction mixture was stirred overnight at room temperature. The reaction mixture was evaporated to dryness, diluted with ethyl acetate, washed successively with water and brine. The organic layer was then dried over anhydrous sodium sulfate, filtered and concentrated in vacuo. The residue was triturated in pentane, filtered and dried to give the title compound methyl 4-chloro-2-{[3-(ethyloxy)-3-oxopropanoyl]amino}-5-iodobenzoate (8.24 g, 19.36 mmol, 75% yield) as beige solid. LCMS: (M+H)+=426; Rt=3.78 min.

Workup

  1. customThe reaction mixture was evaporated to dryness
  2. additiondiluted with ethyl acetate
  3. washwashed successively with water and brine
  4. dry with materialThe organic layer was then dried over anhydrous sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe residue was triturated in pentane
  8. filtrationfiltered
  9. customdried

Sources & evidence

ORD record
ord-d954b8c635354a728a056e55c8a85d48
Source dataset
uspto-grants-2015_06
Patent number
US09061998B2

Reaction notes

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