Dimethyl Sulfide → HCID 67109216, compound

HRID 2370993Notes

Reaction equation

HRID 2370993 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]#[N:12])[C:6]([C:13]1[C:17]([CH3:18])=[CH:16][S:15][C:14]=1[CH3:19])=[C:5]2[C:20]1[CH:25]=[CH:24][C:23]([O:26]C)=[CH:22][CH:21]=1.B(F)(F)F.S(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.CO.[Cl-].[Na+].O>[Cl:1][C:2]1[CH:3]=[C:4]2[C:8](=[CH:9][CH:10]=1)[N:7]([C:11]#[N:12])[C:6]([C:13]1[C:17]([CH3:18])=[CH:16][S:15][C:14]=1[CH3:19])=[C:5]2[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[CH:22][CH:21]=1

Participants

8

Reactant 4

HCID 1068Dimethyl SulfideHCID 6356Boron trifluorideHCID 516892Sodium BicarbonateHCID 67109665HCID 67109665, compound

Product 1

HCID 67109216HCID 67109216, compoundYield 58.3%

Reagents, catalysts & solvents 3

HCID 887MethanolCatalystHCID 6344DichloromethaneSolventHCID 57417360Sodium chloride; waterSolvent

Procedure

5-chloro-2-(2,4-dimethylthiophen-3-yl)-3-(4-methoxyphenyl)-1H-indole-1-carbonitrile (75 mg, 0.19 mmol) was dissolved in 4 ml DCM and the mixture was cooled in an ice bath. BF3.SMe2 (0.20 ml, 1.91 mmol) was added drop wise and the mixture was stirred at room temperature for 24 h. A few drops MeOH were added at 0° C. followed by NaHCO3 (aq, sat) and brine. The layers were separated and the organic layer was concentrated. The crude product was purified on silica (MeOH/DCM 1:99). 42.0 mg 5-chloro-2-(2,4-dimethylthiophen-3-yl)-3-(4-hydroxyphenyl)-1H-indole-1-carbonitrile was obtained.

Workup

  1. temperaturethe mixture was cooled in an ice bath
  2. customThe layers were separated
  3. concentrationthe organic layer was concentrated
  4. customThe crude product was purified on silica (MeOH/DCM 1:99)

Sources & evidence

ORD record
ord-7c37dd2d159845a68140a97ab38887d6
Source dataset
uspto-grants-2014_04
Patent number
US08710243B2

Reaction notes

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