HCID 86619045, compound → Ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate

HRID 1821911Notes

Reaction equation

[Cl:1][C:2]1[CH:7]=[C:6](/[CH:8]=[C:9](\[O-])/[C:10]([O:12][CH2:13][CH3:14])=[O:11])[C:5]([N+:16]([O-])=O)=[CH:4][N:3]=1.[K+]>C(O)(=O)C.[Fe]>[Cl:1][C:2]1[CH:7]=[C:6]2[CH:8]=[C:9]([C:10]([O:12][CH2:13][CH3:14])=[O:11])[NH:16][C:5]2=[CH:4][N:3]=1

Participants

Conditions

Temperature: 60 °C

Procedure

Potassium (1Z)-1-(2-chloro-5-nitropyridin-4-yl)-3-ethoxy-3-oxoprop-1-en-2-olate (2.86 g, 9.20 mmol) was dissolved in acetic acid (140 mL) and iron powder (2.11 g, 37.7 mmol) was added. The mixture was heated at 60° C. for 6 h. The mixture was filtered through a pad of diatomaceous earth and washed with water followed by ethanol. The filtrate was concentrated to dryness. The residue was dissolved in 1:1 methylene chloride/methanol, filtered through a bed of silica gel and washed with 1:1 ethyl acetate/methylene chloride until the filtrate was no longer UV-active. Concentration of the filtrate provided ethyl 5-chloro-1H-pyrrolo[2,3-c]pyridine-2-carboxylate (0.39 g, 19%) as a brown solid: mp 170-175° C. dec.; 1H NMR (300 MHz, CD3OD) δ1.42 (3H, t, J=7.1 Hz), 4.44 (2H, q, J=7.1 Hz), 7.17 (1H, s), 7.72 (1H, s), 8.60 (1H, s); ESI MS m/z 225 [C10H9ClN2O2+H]+; HPLC (Method A) 94.9% (AUC), tR=18.1 min.

Workup

filtrationThe mixture was filtered through a pad of diatomaceous earth
washwashed with water
concentrationThe filtrate was concentrated to dryness
dissolutionThe residue was dissolved in 1:1 methylene chloride/methanol
filtrationfiltered through a bed of silica gel
washwashed with 1:1 ethyl acetate/methylene chloride until the filtrate

Sources & evidence

ORD record: ord-5bcb130e3dfe4a989c026920e1db2195
Source dataset: uspto-grants-2009_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07608627B2

Reaction notes

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