Ethyl Acetate → 6-Fluoro-7-[(methylsulfanyl)methyl]-1H-indole

HRID 561373Notes

Reaction equation

[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([N+:8]([O-])=O)[C:3]=1[CH2:11][S:12][CH3:13].[CH:14]([Mg]Br)=[CH2:15].[Cl-].[NH4+].C(OCC)(=O)C>O1CCCC1>[F:1][C:2]1[C:3]([CH2:11][S:12][CH3:13])=[C:4]2[C:5]([CH:14]=[CH:15][NH:8]2)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: -78 °C

Procedure

A solution of 11.42 g (56.7 mmol) of the compound from Example 2A in 127 ml of tetrahydrofuran was slowly added dropwise to 284 ml (283.7 mmol) of a 0.7N solution of vinylmagnesium bromide in tetrahydrofuran under argon at −78° C., and the solution was then stirred at −78° C. for 2 h. The reaction mixture was added to an ice-cold, saturated aqueous ammonium chloride solution, some ethyl acetate was added, the phases were separated, and the aqueous phase was extracted three times with ethyl acetate. Washing of the combined organic phases with saturated aqueous sodium chloride solution was followed by drying over sodium sulfate, filtration and removal of the solvents in vacuo. Purification of the residue by flash chromatography (mobile phase: cyclohexane/toluene/dichloromethane 10/10/1) afforded 6.31 g (57% of theory) of the title compound.

Workup

customthe phases were separated
extractionthe aqueous phase was extracted three times with ethyl acetate
washWashing of the combined organic phases with saturated aqueous sodium chloride solution
dry with materialby drying over sodium sulfate, filtration and removal of the solvents in vacuo
customPurification of the residue by flash chromatography (mobile phase: cyclohexane/toluene/dichloromethane 10/10/1)

Sources & evidence

ORD record: ord-ae351ae8d6614765ad7b1ed394e33e87
Source dataset: uspto-grants-2011_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08063234B2

Reaction notes

Loading…