4-Fluorothieno[2,3-c]pyridine-2-carboxylic acid → 4-Fluorothieno[2,3-c]pyridine

HRID 389540Notes

Reaction equation

[F:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[S:8][C:9](C(O)=O)=[CH:10][C:3]=12>C1(OC2C=CC=CC=2)C=CC=CC=1.CCCCCCC.[Cu]>[F:1][C:2]1[CH:7]=[N:6][CH:5]=[C:4]2[S:8][CH:9]=[CH:10][C:3]=12

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of 4-fluorothieno[2,3-c]pyridine-2-carboxylic acid (765 mg, 3.88 mmol) and copper powder (629 mg, 9.91 mmol) in diphenyl ether (3.8 mL) was heated to boiling for ˜5 min. After cooling to 40° C., the reaction mixture was diluted with heptane (10 mL), filtered through a short pad of Celite, and concentrated to remove the heptane. Purification of the residue by ISCO chromatography (5 to 45% ethyl acetate:heptane) afforded 441 mg (74%) of the title compound as a white solid. 1H NMR (400 MHz, CDCl3): δ 8.96 (d, J=1.8 Hz, 1 H), 8.34 (d, J=2.0 Hz, 1 H), 7.61-7.88 (m, 1 H), 7.38-7.57 (m, 1 H); MS (ESI): 154.07 [M+H]+; HPLC tR=2.97 min (ZQ3, polar—4 min).

Workup

temperaturewas heated
filtrationfiltered through a short pad of Celite
concentrationconcentrated
customto remove the heptane
customPurification of the residue by ISCO chromatography (5 to 45% ethyl acetate:heptane)

Sources & evidence

ORD record: ord-daf7b9f40d77428c8476c9a12a7b7c19
Source dataset: uspto-grants-2013_02
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08378104B2

Reaction notes

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