Lithium Chloride → HCID 58095104, compound

HRID 2402482Notes

Reaction equation

Br[C:2]1[S:6][C:5]([C:7]2[NH:8][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][N:11]=2)=[C:4]([C:16]2[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=2[Cl:23])[C:3]=1[C:24]#[N:25].C[Sn](C)(C)[C:28]1[CH:33]=[CH:32][N:31]=[C:30]([NH:34][C:35](=[O:37])[CH3:36])[CH:29]=1.[Cl-].[Li+]>O1CCOCC1.[Cu]I.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[C:35]([NH:34][C:30]1[CH:29]=[C:28]([C:2]2[S:6][C:5]([C:7]3[NH:8][C:9]([C:12]([O:14][CH3:15])=[O:13])=[CH:10][N:11]=3)=[C:4]([C:16]3[CH:21]=[CH:20][C:19]([Cl:22])=[CH:18][C:17]=3[Cl:23])[C:3]=2[C:24]#[N:25])[CH:33]=[CH:32][N:31]=1)(=[O:37])[CH3:36]

Participants

Conditions

Temperature: 110 °C

Procedure

Methyl 2-[5-bromo-4-cyano-3-(2,4-dichlorophenyl)-2-thienyl]-1H-imidazole-5-carboxylate (0.216 g, 0.472 mmol), N-[4-(trimethylstannyl)pyridin-2-yl]acetamide (0.170 g, 0.567 mmol), lithium chloride (0.0601 g, 1.42 mmol), copper(I) iodide (0.0270 g, 0.142 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.0273 g, 0.0236 mmol) were combined in dioxane (10 mL) under an atmosphere of Argon. The solution was heated at 110° C. for 3 hours. The solvent was evaporated, and column chromatography was performed to yield the title compound (0.0250 g, 10%). LCMS: (FA) ES+ 513. 1H NMR (300 MHz, d6-DMSO) 8.59-8.57 (m, 1H), 8.54-8.50 (m, 1H), 7.88-7.82 (m, 2H), 7.61-7.58 (m, 2H), 7.56-7.52 (m, 1H), 3.75 (s, 3H), 2.13 (s, 3H).

Workup

customThe solvent was evaporated

Sources & evidence

ORD record: ord-6f9acae9a5484d98804cde2fe8775ec7
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08796314B2

Reaction notes

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