Hydrochloric Acid → HCID 67093326, compound
Reaction equation
Cl.[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[NH:8][C:7]([C:12]1C=N[CH:15]=[CH:16][CH:17]=1)=[C:6]2[CH3:18].CC(C)([O-])C.[K+].C[O:26][C:27](=[O:30])[CH:28]=[CH2:29].Cl.[CH3:32][N:33](C=O)C>>[Cl:2][C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH2:29][CH2:28][C:27]([OH:26])=[O:30])[C:7]([C:12]1[CH:17]=[CH:16][CH:15]=[CH:32][N:33]=1)=[C:6]2[CH3:18]Participants
Conditions
- Temperature
- 0 °C
Procedure
A flask is charged with 5-chloro-3-methyl-2-pyridin-3-yl-1H-indole hydrochloride (Example 2, 0.700 g, 2.50 mmol) in DMF (7 mL) and cooled to 0° C. Potassium tert-butoxide (0.740 mg, 6.26 mmol) is added and the mixture is stirred at room temperature for 30 min, then lowered back into the ice bath. Acrylic acid methyl ester (0.680 mL, 7.52 mmol) is added, and the reaction mixture is stirred for 1.5 h. The reaction mixture is acidified to pH 1 using 1M aqueous HCl and extracted with ethyl acetate. The organic layer is dried over sodium sulfate and concentrated in vacuo to give a residue which is purified by silica gel flash chromatography (dichloromethane-methanol, 9:1) to afford 3-(5-chloro-3-methyl-2-pyridinyl-indol-1-yl)-propionic acid as a white solid. MS (ESI) m/z 315.18 (M+H)+
Workup
- stirringthe reaction mixture is stirred for 1.5 h
- extractionextracted with ethyl acetate
- dry with materialThe organic layer is dried over sodium sulfate
- concentrationconcentrated in vacuo
- customto give a residue which
- customis purified by silica gel flash chromatography (dichloromethane-methanol, 9:1)
Sources & evidence
- ORD record
- ord-422ea6828ca744acbb4ce03210ff9fab
- Source dataset
- uspto-grants-2016_01
- Patent number
- US09242963B2
Reaction notes
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