Triethylsilane → HCID 86727252, compound

HRID 2173056Notes

Reaction equation

HRID 2173056 reaction equation
[Cl:1][C:2]1[C:7]2[C:8](=O)[N:9](CC3C=CC(OC)=CC=3OC)[CH:10]([CH3:11])[C:6]=2[C:5]([F:24])=[C:4]([Cl:25])[N:3]=1.C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O>[Cl:1][C:2]1[C:7]2[CH:8]=[N:9][CH:10]([CH3:11])[C:6]=2[C:5]([F:24])=[C:4]([Cl:25])[N:3]=1

Participants

4

Reactant 2

HCID 12052Triethylsilane2×HCID 86727251HCID 86727251, compound

Product 1

HCID 86727252HCID 86727252, compoundYield 91.6%

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

4,6-Dichloro-2-(2,4-dimethoxybenzyl)-7-fluoro-1-methyl-1H-pyrrolo[3,4-c]pyridin-3(2H)-one (14.0 g, 36.4 mmol) was dissolved in TFA (70 mL) and triethylsilane (5.1 g, 43.7 mmol). The mixture was heated to reflux and additional triethylsilane (1.3 g, 10.9 mmol) was added until the red-colored solution became clear. TFA and triethylsilane were removed under reduced pressure. The mixture was basified with aq. NaHCO3 to pH 7 and filtered to give the title compound (7.3 g, 85%). 1H NMR (DMSO-d6, 400 MHz) δ ppm 1.42 (d, J=6.8 Hz, 3H), 4.92 (q, J=6.8 Hz, 2H), 9.25 (s, 1H). [M+H] calc'd for C8H5C12FN2O, 235. found, 235.

Workup

  1. temperatureThe mixture was heated
  2. temperatureto reflux
  3. customTFA and triethylsilane were removed under reduced pressure
  4. filtrationfiltered

Sources & evidence

ORD record
ord-32f05e6c5a0947b483e13dbc9589a007
Source dataset
uspto-grants-2015_06
Patent number
US09056873B2

Reaction notes

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