6-Bromo-3-pyridinecarboxaldehyde → 6-(7-(2-Fluoro-4-nitrophenoxy)thieno[3,2-b]pyridin-2-yl)nicotinaldehyde

HRID 84375

Reaction equation

[F:1][C:2]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12](I)[S:13][C:6]=12.Br[C:23]1[N:28]=[CH:27][C:26]([CH:29]=[O:30])=[CH:25][CH:24]=1.C[Sn](C)(C)[Sn](C)(C)C>O1CCOCC1>[F:1][C:2]1[CH:18]=[C:17]([N+:19]([O-:21])=[O:20])[CH:16]=[CH:15][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:23]3[CH:24]=[CH:25][C:26]([CH:29]=[O:30])=[CH:27][N:28]=3)[S:13][C:6]=12

Participants

Conditions

Temperature: 100 °C

Procedure

To a solution of 7-(2-fluoro-4-nitrophenoxy)-2-iodothieno[3,2-b]pyridine (24) [US 2006/0287343 A1] (6 g, 14.42 mmol) in dioxane (40 mL) were added 6-bromopyridine-3-carbaldehyde (3.22 g, 17.30 mmol), palladium tetrakistriphenylphosphine (0.500 g, 0.433 mmol) and hexamethyldistannane (3.29 mL, 15.86 mmol). The mixture was heated at 100° C. for 20 h. It was then concentrated and adsorbed on silica gel, transferred onto a silica gel column and eluted with DCM/MeOH (100/0, 99/1, 98/2, 97/3) to afford title compound 123 (2.864 g, 50% yield). MS (m/z): 396.1 (M+H).

Workup

concentrationIt was then concentrated
washeluted with DCM/MeOH (100/0, 99/1, 98/2, 97/3)

Sources & evidence

ORD record: ord-af4c3697ce7a4cc692ebf431b4df3f46
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08846927B2

Linked notes

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