methyl[5-chloro-2-(4-ethyl-3-fluoropyridine-2-carbonyl)-1H-indol-3-yl]acetate → [5-Chloro-2-(4-ethyl-3-fluoropyridine-2-carbonyl)-1H-indol-3-yl]acetic Acid

HRID 396495Notes

Reaction equation

HRID 396495 reaction equation
C[O:2][C:3](=[O:26])[CH2:4][C:5]1[C:13]2[C:8](=[CH:9][CH:10]=[C:11]([Cl:14])[CH:12]=2)[NH:7][C:6]=1[C:15]([C:17]1[C:22]([F:23])=[C:21]([CH2:24][CH3:25])[CH:20]=[CH:19][N:18]=1)=[O:16]>C(O)(=O)C.Cl>[Cl:14][C:11]1[CH:12]=[C:13]2[C:8](=[CH:9][CH:10]=1)[NH:7][C:6]([C:15]([C:17]1[C:22]([F:23])=[C:21]([CH2:24][CH3:25])[CH:20]=[CH:19][N:18]=1)=[O:16])=[C:5]2[CH2:4][C:3]([OH:26])=[O:2]

Participants

4

Reactant 1

HCID 23003366methyl[5-chloro-2-(4-ethyl-3-fluoropyridine-2-carbonyl)-1H-indol-3-yl]acetate

Product 1

HCID 18542322[5-Chloro-2-(4-ethyl-3-fluoropyridine-2-carbonyl)-1H-indol-3-yl]acetic AcidYield 93%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 313Hydrochloric AcidSolvent

Procedure

A stirred solution of methyl[5-chloro-2-(4-ethyl-3-fluoropyridine-2-carbonyl)-1H-indol-3-yl]acetate (Example 111, 391.2 mg, 1.044 mmol) in acetic acid (12 ml) and 2N aqueous HCl (4 ml) was heated at reflux temperature for 24 h. After cooling to room temperature, the resulting mixture was concentrated. The residue was diluted in THF (100 ml), dried (MgSO4) and concentrated. The crude product was purified by recrystallization to afford 349.2 mg (93%) of the title compound.

Workup

  1. temperatureat reflux temperature for 24 h
  2. concentrationthe resulting mixture was concentrated
  3. additionThe residue was diluted in THF (100 ml)
  4. dry with materialdried (MgSO4)
  5. concentrationconcentrated
  6. customThe crude product was purified by recrystallization

Sources & evidence

ORD record
ord-489dbe877c0d4f6698843ec78e7566a7
Source dataset
uspto-grants-2003_08
Patent number
US06608070B1

Reaction notes

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