Sodium Carbonate → Methyl 5-bromo-3-(tetrahydro-2H-thiopyran-4-yl)-1H-indole-7-carboxylate
Reaction equation
[Si](OS(C(F)(F)F)(=O)=O)(C)(C)C.[S:13]1[CH2:18][CH2:17][C:16](=O)[CH2:15][CH2:14]1.[Br:20][C:21]1[CH:22]=[C:23]2[C:27](=[C:28]([C:30]([O:32][CH2:33]C)=[O:31])[CH:29]=1)[NH:26][CH:25]=[CH:24]2.C([SiH](CC)CC)C.C([O-])([O-])=O.[Na+].[Na+]>C(Cl)Cl>[Br:20][C:21]1[CH:22]=[C:23]2[C:27](=[C:28]([C:30]([O:32][CH3:33])=[O:31])[CH:29]=1)[NH:26][CH:25]=[C:24]2[CH:16]1[CH2:17][CH2:18][S:13][CH2:14][CH2:15]1Participants
Reactant 5
Product 1
Reagents, catalysts & solvents 1
Procedure
TMSOTf (2.1 mL, 11.8 mmol) was added dropwise over 2.25 min to a solution of tetrahydro-4H-thiopyran-4-one (0.686 g, 5.9 mmol) in DCM (75 mL) at 0° C. (bath temp). A solution of ethyl 5-bromo-1H-indole-7-carboxylate (1.5 g, 5.9 mmol) in DCM (25 mL) was added dropwise via addition funnel over 20 min. Triethylsilane (3.76 mL, 23.6 mmol) was added in one portion and the reaction was allowed to warm to room temperature over 15 h. Saturated aqueous Na2CO3 (35 mL) was added, the layers were separated and the aqueous layer was extracted with DCM (1×75 mL). The combined organic layers were concentrated under reduced pressure, the crude product was washed with MeOH (2×8 mL) and dried under high vacuum, giving 1.59 g (76%) of the title compound.
Workup
- customthe layers were separated
- extractionthe aqueous layer was extracted with DCM (1×75 mL)
- concentrationThe combined organic layers were concentrated under reduced pressure
- washthe crude product was washed with MeOH (2×8 mL)
- customdried under high vacuum
Sources & evidence
- ORD record
- ord-dbbad270cb2c4b8ea56bd619c05c7fc4
- Source dataset
- uspto-grants-2013_02
- Patent number
- US08372875B2
Reaction notes
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