Trifluoroacetic acid → HCID 11566711, compound

HRID 1631475Notes

Reaction equation

HRID 1631475 reaction equation
C[O:2][C:3](=[O:16])[CH2:4][C:5]1[C:13]2[C:8](=[N:9][CH:10]=[CH:11][CH:12]=2)[NH:7][C:6]=1[CH2:14][CH3:15].C([SiH](CC)CC)C.CO[C:26](=O)[C:27]([C:29]1[C:37]2C(=NC=CC=2)N[C:30]=1[CH2:38]C)=O.[C:41](O)([C:43]([F:46])([F:45])[F:44])=O>>[CH2:14]([C:6]1[N:7]([CH2:37][C:29]2[CH:30]=[CH:38][C:41]([C:43]([F:46])([F:45])[F:44])=[CH:26][CH:27]=2)[C:8]2=[N:9][CH:10]=[CH:11][CH:12]=[C:13]2[C:5]=1[CH2:4][C:3]([OH:2])=[O:16])[CH3:15]

Participants

5

Reactant 4

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 67218912HCID 67218912, compoundHCID 67219373HCID 67219373, compound

Product 1

HCID 11566711HCID 11566711, compound

Procedure

(2-Ethyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-acetic acid methyl ester: To a solution of triethylsilane (818 μl, 5.12 mmol) in TFA (1.6 ml) at −10° C. is added portion wise (2-ethyl-1 H-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-6eed2c19342c4fd182eba30f5238f061
Source dataset
uspto-grants-2014_07
Patent number
US08791256B2

Reaction notes

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