Water → 7-Bromo-2-phenylthieno[3,2-c]pyridin-4(5H)-one

HRID 1868324Notes

Reaction equation

[C:1]1([C:7]2[S:15][C:14]3[CH:13]=[CH:12][NH:11][C:10](=[O:16])[C:9]=3[CH:8]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.C1C(=O)N([Br:24])C(=O)C1.O>CN(C=O)C>[Br:24][C:13]1[C:14]2[S:15][C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[CH:8][C:9]=2[C:10](=[O:16])[NH:11][CH:12]=1

Participants

Conditions

Temperature: 60 °C

Procedure

To compound 2 (3.92 g, 17.24 mmol) in DMF (133 mL) was added NBS (3.37 g, 19.0 mmol). The solution was heated to 60° C. After 1 h, the solution volume was reduced to approximately one half the volume, and the solution was poured into H2O (700 mL). The precipitate was filtered, washed with water, and dried to yield 5.08 g of 3. 1H NMR (400 MHz, d6-DMSO) δ: 11.84 (s, 1H), 8.05 (s, 1H), 7.82 (d, J=7 Hz, 2H), 7.61 (s, 1H), 7.48 (t, J=7 Hz 2H), 7.4 (t, J=7 Hz, 1H).

Workup

filtrationThe precipitate was filtered
washwashed with water
customdried

Sources & evidence

ORD record: ord-4d04a666af86495ea0bedbba01129a5b
Source dataset: uspto-grants-2009_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07635695B2

Reaction notes

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