Potassium Carbonate → (E)-ethyl 3-(4-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)acrylate

HRID 336879Notes

Reaction equation

[Cl:1][C:2]1[C:7]([CH:8]=O)=[CH:6][N:5]=[C:4]2[N:10]([Si](C(C)C)(C(C)C)C(C)C)[CH:11]=[CH:12][C:3]=12.C([O-])([O-])=[O:24].[K+].[K+].[O:29]1[CH2:34][CH2:33]O[CH2:31][CH2:30]1>CCOC(C)=O>[Cl:1][C:2]1[C:7](/[CH:8]=[CH:31]/[C:30]([O:29][CH2:34][CH3:33])=[O:24])=[CH:6][N:5]=[C:4]2[NH:10][CH:11]=[CH:12][C:3]=12

Participants

Conditions

Temperature: 80 °C

Procedure

To a solution of compound 4.0 4-chloro-1-(triisopropylsilyl)-1H-pyrrolo[2,3-b]pyridine-5-carbaldehyde (1.7 g, 5 mmol, 1 equiv.) in dioxane (20 mL) at room temperature was added triethyl phosphonoacetate (3 mL, 15 mmol, 3 equiv.) and K2CO3 (3.45 g, 25 mmol, 5 equiv.). The resulting mixture was heated overnight at 80° C. under argon. Upon cooling to room temperature, the mixture was diluted with EtOAc (50 mL) and washed with water (50 mL) and brine (50 mL). The organic phase was dried over Na2SO4, after removal of solvent under vacuum. The resulting residue was purified with flash chromatography (Hexanes: EtOAc=6:1) to afford the desired product 4.1 (E)-ethyl 3-(4-chloro-1H-pyrrolo[2,3-b]pyridin-5-yl)acrylate (0.63g; 50%). LC-MS:(M+H) 251.29

Workup

temperatureUpon cooling to room temperature
washwashed with water (50 mL) and brine (50 mL)
dry with materialThe organic phase was dried over Na2SO4
customafter removal of solvent under vacuum
customThe resulting residue was purified with flash chromatography (Hexanes: EtOAc=6:1)

Sources & evidence

ORD record: ord-88837411efc847288ecca5b77efdb78a
Source dataset: uspto-grants-2014_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08889706B2

Reaction notes

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