6-Bromoindole → HCID 89526381, compound
Reaction equation
Br[C:2]1[CH:10]=[C:9]2[C:5]([CH:6]=[CH:7][NH:8]2)=[CH:4][CH:3]=1.[CH3:11][O:12][C:13](=[O:19])[CH2:14][CH2:15][S:16]([O-:18])=[O:17].[Na+]>[Cu]I>[NH:8]1[C:9]2[C:5](=[CH:4][CH:3]=[C:2]([S:16]([CH2:15][CH2:14][C:13]([O:12][CH3:11])=[O:19])(=[O:18])=[O:17])[CH:10]=2)[CH:6]=[CH:7]1Participants
4
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 110 °C
Procedure
6-bromo-1H-indole (3.0 g, 15.3 mmol), sodium 3-methoxy-3-oxopropane-1-sulfinate (8.0 g, 45.9 mmol) and CuI (14.6 g, 77.0 mmol) were charged to a sealable flask. The flask was closed and degassed twice, and then dry DMSO (30 mL) was added and the reaction mixture degassed again before being heated at 110° C. in an oil bath overnight. The reaction mixture was cooled and diluted with ethyl acetate (300 mL). The mixture was filtered on a silica gel pad and eluted with ethyl acetate. The organic phase was concentrated under reduced pressure. The crude was purified on silica gel eluting with hexanes and ethyl acetate, then with DCM and methanol to afford the title compound.
Workup
- customThe flask was closed
- customdegassed twice
- additiondry DMSO (30 mL) was added
- customthe reaction mixture degassed again
- temperatureThe reaction mixture was cooled
- additiondiluted with ethyl acetate (300 mL)
- filtrationThe mixture was filtered on a silica gel pad
- washeluted with ethyl acetate
- concentrationThe organic phase was concentrated under reduced pressure
- customThe crude was purified on silica gel eluting with hexanes and ethyl acetate
Sources & evidence
- ORD record
- ord-fc80e878381e4999b89588236a65eb2e
- Source dataset
- uspto-grants-2015_09
- Patent number
- US09133157B2
Reaction notes
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