Dimethyl Sulfide → HCID 67108811, compound

HRID 2370997Notes

Reaction equation

HRID 2370997 reaction equation
[CH3:1][C:2]1[C:6]([C:7]2[N:8]([C:24]#[N:25])[C:9]3[C:14]([C:15]=2[C:16]2[CH:21]=[CH:20][C:19]([O:22]C)=[CH:18][CH:17]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:26])[S:4][N:3]=1.B(F)(F)F.S(C)C.C([O-])(O)=O.[Na+]>C(Cl)Cl.CO>[CH3:1][C:2]1[C:6]([C:7]2[N:8]([C:24]#[N:25])[C:9]3[C:14]([C:15]=2[C:16]2[CH:21]=[CH:20][C:19]([OH:22])=[CH:18][CH:17]=2)=[CH:13][CH:12]=[CH:11][CH:10]=3)=[C:5]([CH3:26])[S:4][N:3]=1

Participants

7

Reactant 4

HCID 1068Dimethyl SulfideHCID 6356Boron trifluorideHCID 516892Sodium BicarbonateHCID 67109272HCID 67109272, compound

Product 1

HCID 67108811HCID 67108811, compoundYield 47.4%

Reagents, catalysts & solvents 2

HCID 887MethanolCatalystHCID 6344DichloromethaneSolvent

Conditions

Temperature
1 °C

Procedure

2-(3,5-dimethylisothiazol-4-yl)-3-(4-methoxyphenyl)-1H-indole-1-carbonitrile (38 mg, 0.11 mmol) was dissolved in 10 ml DCM and the mixture was cooled in an ice bath. BF3.SMe2 (0.56 ml, 5.29 mmol) was added drop wise and the mixture was stirred at 0-2° C. for 16 h. A few drops MeOH were added followed by NaHCO3 (aq, sat). The layers were separated and the organic layer was concentrated. The crude product was purified by preparative HPLC. 18.0 mg 2-(3,5-dimethylisothiazol-4-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 by preparative HPLC

Sources & evidence

ORD record
ord-234f5d35a471443b86e7568f1127c9d9
Source dataset
uspto-grants-2014_04
Patent number
US08710243B2

Reaction notes

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