Triethylsilane → HCID 90408840, compound

HRID 2177616Notes

Reaction equation

HRID 2177616 reaction equation
[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[C:10]([N:12]1[CH:17]=[CH:16][C:15]2[N:18]([C:21]3[CH:26]=[N:25][CH:24]=[CH:23][N:22]=3)[N:19]=[N:20][C:14]=2[CH:13]1[CH3:27])=[O:11].C([SiH](CC)CC)C>C(O)(C(F)(F)F)=O.C(Cl)Cl>[Cl:1][C:2]1[C:7]([Cl:8])=[C:6]([F:9])[CH:5]=[CH:4][C:3]=1[C:10]([N:12]1[CH2:17][CH2:16][C:15]2[N:18]([C:21]3[CH:26]=[N:25][CH:24]=[CH:23][N:22]=3)[N:19]=[N:20][C:14]=2[CH:13]1[CH3:27])=[O:11]

Participants

5

Reactant 2

HCID 12052TriethylsilaneHCID 90409018HCID 90409018, compound

Product 1

HCID 90408840HCID 90408840, compoundYield 40%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 6422Trifluoroacetic acidSolvent

Conditions

Temperature
80 °C

Procedure

To a solution of the product of Example 140, Step 1 (350 mg, 0.864 mmol) in TFA (2 mL) was added triethylsilane (0.35 mL, 2.16 mmol). The reaction was sealed and heated at 80° C. for 2 h. The reaction was diluted with CH2Cl2 and the organic portion washed with NaHCO3. The organic portion was then dried over Na2SO4, concentrated and purified by chromatography on silica gel eluted with heptane/EtOAc to afford the title compound (140 mg, 40%) MS (ESI) mass calcd. C17H13Cl2FN6O 406.1. m/z found, 407.0 [M+H]+.

Workup

  1. customThe reaction was sealed
  2. washthe organic portion washed with NaHCO3
  3. dry with materialThe organic portion was then dried over Na2SO4
  4. concentrationconcentrated
  5. custompurified by chromatography on silica gel
  6. washeluted with heptane/EtOAc

Sources & evidence

ORD record
ord-aa0cb3f1c2ed40dba6c321bb643177db
Source dataset
uspto-grants-2015_06
Patent number
US09066946B2

Reaction notes

Loading…