Triethylsilane → methyl 2-(6-chloro-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)acetate

HRID 1260653Notes

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][C:18]([Cl:22])=[CH:19][CH:20]=2)[NH:15][C:14]=1[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][C:18]([Cl:22])=[CH:19][CH:20]=2)[NH:15][C:14]=1[CH3:23]

Participants

Conditions

Temperature: -10 °C

Procedure

To a solution of triethylsilane (0.343 ml, 2.15 mmol) in TFA (2 ml) cooled to −10° C. is added portionwise (6-chloro-2-methyl-1H-pyrrolo[2,3-b]pyridin-3-yl)-oxo-acetic acid methyl ester (0.155 g, 0.61 mmol). The reaction mixture is stirred at −10° C. for 1 hour and the solvent is removed in vacuo. The residue is washed with saturated sodium hydrogen carbonate solution and this aqueous portion is extracted with DCM (3×10 ml). The organics are combined, dried (Na2SO4) and concentrated in vacuo and the resulting crude is purified by chromatography on silica eluting with methanol/DCM (0-0.5% methanol) to yield the titled product as an off-white powder. (MH+ 239).

Workup

customthe solvent is removed in vacuo
washThe residue is washed with saturated sodium hydrogen carbonate solution
extractionthis aqueous portion is extracted with DCM (3×10 ml)
dry with materialdried (Na2SO4)
concentrationconcentrated in vacuo
customthe resulting crude is purified by chromatography on silica eluting with methanol/DCM (0-0.5% methanol)

Sources & evidence

ORD record: ord-a243922639e74d368f5cd13cb4bfe710
Source dataset: uspto-grants-2013_06
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08470848B2

Reaction notes

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