Lithium Chloride → HCID 58095104, compound

HRID 2282156Notes

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-997348dd019f4b64a60652a3210ee76a
Source dataset: uspto-grants-2015_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09139589B2

Reaction notes

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