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

HRID 1944602Notes

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 (0.63 g; 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-b4a449153b8245ecbafd72c5fa02982e
Source dataset: uspto-grants-2013_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08394818B2

Reaction notes

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