Methyl 5-nitro-2-[3-(tetrahydropyran-2-yloxy)-propyl]-1H-indole-4-carboxylate → methyl 2-(3-hydroxypropyl)-5-nitro-1H-indole-4-carboxylate
Reaction equation
[N+:1]([C:4]1[CH:12]=[CH:11][C:10]2[NH:9][C:8]([CH2:13][CH2:14][CH2:15][O:16]C3CCCCO3)=[CH:7][C:6]=2[C:5]=1[C:23]([O:25][CH3:26])=[O:24])([O-:3])=[O:2]>Cl.CO>[OH:16][CH2:15][CH2:14][CH2:13][C:8]1[NH:9][C:10]2[CH:11]=[CH:12][C:4]([N+:1]([O-:3])=[O:2])=[C:5]([C:23]([O:25][CH3:26])=[O:24])[C:6]=2[CH:7]=1Participants
4
Procedure
Methyl 5-nitro-2-[3-(tetrahydropyran-2-yloxy)-propyl]-1H-indole-4-carboxylate (Intermediate 22, 0.650 g) was dissolved in a solution of hydrogen chloride in methanol (1.25M, 18 ml) and the resultant mixture was stirred at room temperature for 1 hour. The mixture was concentrated in vacuo and the residue was partitioned between ethyl acetate and aqueous potassium carbonate solution (10%). The aqueous layer was extracted with ethyl acetate and the combined organic layers were washed with brine, dried (MgSO4) and filtered. The filtrate was concentrated in vacuo to give methyl 2-(3-hydroxypropyl)-5-nitro-1H-indole-4-carboxylate (0.388 g) as a dark orange gum.
Workup
- concentrationThe mixture was concentrated in vacuo
- customthe residue was partitioned between ethyl acetate and aqueous potassium carbonate solution (10%)
- extractionThe aqueous layer was extracted with ethyl acetate
- washthe combined organic layers were washed with brine
- dry with materialdried (MgSO4)
- filtrationfiltered
- concentrationThe filtrate was concentrated in vacuo
Sources & evidence
- ORD record
- ord-6b3ce522fb034301be9e8c8790456c12
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09187494B2
Reaction notes
Loading…