Dimethylformamide → 5-(3,4-diethoxyphenyl)-3-(1H-pyrrolo[2,3-b]pyridin-4-yl)-1,2,4-oxadiazole
Reaction equation
[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[C:7]([OH:9])=O)[CH3:2].CC[N:18]=[C:19]=[N:20]CCCN(C)C.[CH:27]1[CH:28]=[CH:29][C:30]2[N:35](O)N=[N:33][C:31]=2[CH:32]=1.[CH3:37]N(C=O)C>>[CH2:1]([O:3][C:4]1[CH:5]=[C:6]([C:7]2[O:9][N:20]=[C:19]([C:28]3[CH:29]=[CH:30][N:35]=[C:37]4[NH:33][CH:31]=[CH:32][C:27]=34)[N:18]=2)[CH:10]=[CH:11][C:12]=1[O:13][CH2:14][CH3:15])[CH3:2]Participants
Procedure
To a stirred solution of 3,4-diethoxybenzoic acid (50 mg, 0.24 mmol) in DMF was added EDCI (59 mg, 0.31 mmol) and HOBt (41 mg, 0.31 mmol), the reaction was stirred 20 min at room temperature. To the reaction was added the N′-hydroxyimidamide (54 mg, 0.31 mmol) and the mixture was stirred for 30 min at room temperature followed by 16 h at 95° C. The reaction was concentrated under reduced pressure, diluted with EtOAc (80 ml) and washed with a saturated solution of NaHCO3 (2×30 ml) and brine (50 ml). The organic layer was dried over Na2SO4 and concentrated under reduced pressure. The crude was purified by column chromatography using CH2Cl2:MeOH (9:1) to offer the product as a brown solid in 5% yield (4 mg, 0.01 mmol). MS (EI) m/z: 351 (M+)
Workup
- stirringthe mixture was stirred for 30 min at room temperature
- waitfollowed by 16 h at 95° C
- concentrationThe reaction was concentrated under reduced pressure
- additiondiluted with EtOAc (80 ml)
- washwashed with a saturated solution of NaHCO3 (2×30 ml) and brine (50 ml)
- dry with materialThe organic layer was dried over Na2SO4
- concentrationconcentrated under reduced pressure
- customThe crude was purified by column chromatography
Sources & evidence
- ORD record
- ord-cff60ab2e3f54785969c3e3f35a9fece
- Source dataset
- uspto-grants-2014_08
- Patent number
- US08796318B2
Reaction notes
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