Acetic Acid → 2-Iodo-4-oxo-4,5-dihydro-thieno[3,2-c]pyridine-7-carbonitrile

HRID 1868293Notes

Reaction equation

[O:1]=[C:2]1[C:7]2[CH:8]=[CH:9][S:10][C:6]=2[C:5]([C:11]#[N:12])=[CH:4][NH:3]1.C(O)(=O)C.[I:17]N1C(=O)CCC1=O.C(=O)(O)[O-].[Na+]>O.CN(C=O)C>[I:17][C:9]1[S:10][C:6]2[C:5]([C:11]#[N:12])=[CH:4][NH:3][C:2](=[O:1])[C:7]=2[CH:8]=1

Participants

Conditions

Temperature: 80 °C

Procedure

To 4-oxo-4,5-dihydro-thieno[3,2-c]pyridine-7-carbonitrile 24 (5 g, 28.4 mmol) in a 1:1 solution of acetic acid and DMF (18.4 mL) was added N-iodosuccinimide (12.8 g, 56.8 mmol). The reaction was warmed to 80° C. and stirred for 21 h. The reaction was diluted 10 fold with water and neutralized with aqueous sodium bicarbonate. The precipitate was filtered, washed with water and dried to provide 7.27 g of 25. 1H NMR (400 MHz, d6-DMSO) δ 12.45 (s, 1H), 8.25 (d, J=5 Hz, 1H), 7.77 (s, 1H).

Workup

filtrationThe precipitate was filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-383d1c5e9262487e8e19ae0e92535074
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635695B2

Reaction notes

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