Triethylsilane → HCID 67219373, compound

HRID 1445589Notes

Reaction equation

HRID 1445589 reaction equation
C([SiH](CC)CC)C.[CH3:8][O:9][C:10](=[O:24])[C:11]([C:13]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[NH:15][C:14]=1[CH2:22][CH3:23])=O>C(O)(C(F)(F)F)=O>[CH3:8][O:9][C:10](=[O:24])[CH2:11][C:13]1[C:21]2[C:16](=[N:17][CH:18]=[CH:19][CH:20]=2)[NH:15][C:14]=1[CH2:22][CH3:23]

Participants

4

Reactant 2

HCID 12052TriethylsilaneHCID 67218912HCID 67218912, compound

Product 1

HCID 67219373HCID 67219373, compound

Reagents, catalysts & solvents 1

HCID 6422Trifluoroacetic acidSolvent

Procedure

To a solution of triethylsilane (818 μl, 5.12 mmol) in TFA (1.6 ml) at −10° C. is added portion wise (2-ethyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-oxo-acetic acid methyl ester (0.34 g, 1.46 mmol). After stirring at room temperature overnight, the solvent is removed in vacuo and the resulting residue is neutralized with saturated sodium bicarbonate solution. The solution is extracted with DCM (3×20 ml) and the organic portions are combined, dried (Na2SO4) and concentrated in vacuo. The residue is loaded on a pre-packed Isolute™ silica column and eluted with DCM/MeOH (100:0 increasing to 98:2) to yield the titled compound as a yellow powder. (MH+ 219)

Workup

  1. customthe solvent is removed in vacuo
  2. extractionThe solution is extracted with DCM (3×20 ml)
  3. dry with materialdried (Na2SO4)
  4. concentrationconcentrated in vacuo
  5. washeluted with DCM/MeOH (100:0 increasing to 98:2)

Sources & evidence

ORD record
ord-7a762967a4184dc99435bd070a48425c
Source dataset
uspto-grants-2010_02
Patent number
US07666878B2

Reaction notes

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