Hydrochloric Acid → 2-Ethoxycarbonylmethyl-1-(4-isopropoxyphenyl)-5-(5-trifluoromethyl-2-pyridinyloxy)indole-3-carboxylic acid
Reaction equation
[C:1]([CH2:4][C:5]1[N:6]([C:28]2[CH:33]=[CH:32][C:31]([O:34][CH:35]([CH3:37])[CH3:36])=[CH:30][CH:29]=2)[C:7]2[C:12]([C:13]=1[C:14]([OH:16])=[O:15])=[CH:11][C:10]([O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=1)=[CH:9][CH:8]=2)([OH:3])=[O:2].Cl.[CH3:39][CH2:40]O>>[CH2:39]([O:2][C:1]([CH2:4][C:5]1[N:6]([C:28]2[CH:29]=[CH:30][C:31]([O:34][CH:35]([CH3:37])[CH3:36])=[CH:32][CH:33]=2)[C:7]2[C:12]([C:13]=1[C:14]([OH:16])=[O:15])=[CH:11][C:10]([O:17][C:18]1[CH:23]=[CH:22][C:21]([C:24]([F:27])([F:26])[F:25])=[CH:20][N:19]=1)=[CH:9][CH:8]=2)=[O:3])[CH3:40]Participants
4
Procedure
A mixture of 2-carboxymethyl-1-(4-isopropoxyphenyl)-5-(5-trifluoromethyl-2-pyridinyloxy)indole-3-carboxylic acid (85 mg, 0.16 mmol, see Example 26), EtOH (0.8 mL) and HCl (1 M in EtOH, 0.1 mL) was heated at reflux for 20 min, concentrated, diluted with water, neutralized with NaHCO3 (aq, sat) and extracted with EtOAc. The organic layer was washed with brine, dried (Na2SO4), concentrated and purified by chromatography to give the title compound. Yield 45 mg (52%), mp 202° C.
Workup
- temperaturewas heated
- temperatureat reflux for 20 min
- concentrationconcentrated
- additiondiluted with water
- extractionextracted with EtOAc
- washThe organic layer was washed with brine
- dry with materialdried (Na2SO4)
- concentrationconcentrated
- custompurified by chromatography
Sources & evidence
- ORD record
- ord-c6255b18a23b4f748579872f8eacd0f7
- Source dataset
- uspto-grants-2012_01
- Patent number
- US08097623B2
Reaction notes
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