Dimethylcarbamoyl Chloride → HCID 86689854, compound

HRID 2409039Notes

Reaction equation

HRID 2409039 reaction equation
[F:1][C:2]1[CH:3]=[C:4]2[N:11]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:10]=[CH:9][C:5]2=[N+:6]([O-])[CH:7]=1.[CH3:22][N:23](C)C(Cl)=O.C[Si](C#N)(C)C>ClCCCl>[F:1][C:2]1[CH:3]=[C:4]2[N:11]([S:12]([C:15]3[CH:21]=[CH:20][C:18]([CH3:19])=[CH:17][CH:16]=3)(=[O:14])=[O:13])[CH:10]=[CH:9][C:5]2=[N:6][C:7]=1[C:22]#[N:23]

Participants

5

Reactant 3

HCID 6598Dimethylcarbamoyl ChlorideHCID 82115Trimethylsilyl cyanideHCID 86689852HCID 86689852, compound

Product 1

HCID 86689854HCID 86689854, compoundYield 44.5%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of 6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridine 4-oxide (2.4 g, 7.84 mmol) in 1,2-dichloroethane (60 mL) was added dimethylcarbamic chloride (1.3 g, 11.76 mmol), followed by addition of trimethylsilyl cyanide (1.2 g, 11.76 mmol). The mixture was stirred under nitrogen at 80° C. overnight. The resulting mixture was quenched by addition of a sat'd aq. NaHCO3 solution. The organic layer was washed with H2O (50 mL×3) and concentrated under reduced pressure. The crude product was purified by SiO2 chromatography eluting with petroleum ether/EtOAc (4:1) as eluent to afford 1.1 g (44.5%) of 6-fluoro-1-tosyl-1H-pyrrolo[3,2-b]pyridine-5-carbonitrile. MS (ESI) m/z: 316.1 [M+1]+.

Workup

  1. customThe resulting mixture was quenched by addition of a sat'd aq. NaHCO3 solution
  2. washThe organic layer was washed with H2O (50 mL×3)
  3. concentrationconcentrated under reduced pressure
  4. customThe crude product was purified by SiO2 chromatography
  5. washeluting with petroleum ether/EtOAc (4:1) as eluent

Sources & evidence

ORD record
ord-518f910dbf3c4fd290430eeb26c50b17
Source dataset
uspto-grants-2014_08
Patent number
US08815877B2

Reaction notes

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