Lithium Chloride → HCID 178474051, compound

HRID 1530138Notes

Reaction equation

Br[C:2]1[S:3][C:4]([C:15]2[NH:16][CH:17]=[C:18]([CH3:20])[N:19]=2)=[C:5]([C:7]2[CH:12]=[CH:11][C:10]([Cl:13])=[CH:9][C:8]=2[Cl:14])[N:6]=1.C[Sn](C)(C)[C:23]1[CH:28]=[CH:27][N:26]=[C:25]([NH:29][C:30](=[O:32])[CH3:31])[CH:24]=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>[Cl:14][C:8]1[CH:9]=[C:10]([Cl:13])[CH:11]=[CH:12][C:7]=1[C:5]1[N:6]=[C:2]([C:23]2[CH:28]=[CH:27][N:26]=[C:25]([NH:29][C:30](=[O:32])[CH3:31])[CH:24]=2)[S:3][C:4]=1[C:15]1[NH:16][CH:17]=[C:18]([CH3:20])[N:19]=1

Participants

Conditions

Temperature: 90 °C

Procedure

2-bromo-4-(2,4-dichlorophenyl)-5-(4-methyl-1H-imidazol-2-yl)-1,3-thiazole (55 mg, 0.141 mmol), N-[4-(trimethylstannyl)pyridin-2-yl]acetamide (64 mg, 0.214 mmol) were dissolved in 1,4-dioxane (3.4 mL). Lithium chloride (18.1 mg, 0.427 mmol), copper(I) iodide (8.14 mg, 0.0427 mmol) and tetrakis(triphenylphosphine)palladium(0) (8.23 mg, 0.00712 mmol) were added under atmosphere of argon. The reaction mixture was heated at 90° C. for 7 hours. LCMS indicated complete conversion. Solvent was evaporated and the residue was purified using preparative HPLC to afford 15 mg of the title compound (24%). LCMS; (AA) ES+ 444, 446. 1H NMR (400 MHz, d1-chloroform) δ: 8.79-8.70 (m, 1H), 8.43 (s, 1H), 8.35-8.28 (m, 1H), 7.62-7.59 (m, 2H), 7.50 (d, J=8.25 Hz, 1H), 7.43 (dd, J=8.23, 2.01 Hz, 1H), 2.24 (s, 3H), 2.20 (s, 3H).

Workup

customSolvent was evaporated
customthe residue was purified

Sources & evidence

ORD record: ord-48598f1ee4194fb9a4b8f71a9a605f54
Source dataset: uspto-grants-2015_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09090601B2

Reaction notes

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