Acetic Acid → ethyl 1-methyl-6-(phenylsulfonyl)-6H-pyrrolo[2,3-e][1,2,4]triazolo[4,3-a]pyridine-7-carboxylate
Reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:14]([S:15]([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)(=[O:17])=[O:16])[C:13]2[C:8](=[N:9][C:10]([N:24](C(OC(C)(C)C)=O)[NH:25][C:26](OC(C)(C)C)=O)=[CH:11][CH:12]=2)[CH:7]=1)=[O:5])[CH3:2].[CH3:40]C(O)=O>>[CH3:40][C:26]1[N:9]2[C:8]3[CH:7]=[C:6]([C:4]([O:3][CH2:1][CH3:2])=[O:5])[N:14]([S:15]([C:18]4[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=4)(=[O:16])=[O:17])[C:13]=3[CH:12]=[CH:11][C:10]2=[N:24][N:25]=1Participants
3
Conditions
- Temperature
- 180 °C
Procedure
A solution of di-tert-butyl 1-[2-(ethoxycarbonyl)-1-(phenylsulfonyl)-1H-pyrrolo[3,2-b]pyridin-5-yl]hydrazine-1,2-dicarboxylate (2.5 g, 4.4 mmol, from Step 2) in AcOH (40 mL) was split into 5 batches and each was heated in the microwave to a temperature of 180° C. for 3 minutes. The reaction contents were pooled and AcOH was removed in vacuo. The residue was dissolved in EtOAc and washed with sat′d NaHCO3 solution, followed by brine. The organic layer was dried over sodium sulfate, filtered and concentrated. Flash chromatography, eluting with a gradient from 0-100% EtOAc in hexanes, followed by 10% MeOH in DCM as mobile phase afforded solid product (1.27 g, 74%).
Workup
- customThe reaction contents
- customAcOH was removed in vacuo
- dissolutionThe residue was dissolved in EtOAc
- washwashed with sat′d NaHCO3 solution
- dry with materialThe organic layer was dried over sodium sulfate
- filtrationfiltered
- concentrationconcentrated
- washFlash chromatography, eluting with a gradient from 0-100% EtOAc in hexanes
Sources & evidence
- ORD record
- ord-e9d02ef8dd7942fbb1ab65ed768d01c9
- Source dataset
- uspto-grants-2016_04
- Patent number
- US09309246B2
Reaction notes
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