Trimethylsilylacetylene → 3,4-difluoro-2-[2-fluoro-4-(2-trimethylsilylethynyl)anilino]-N-(2-hydroxyethoxy)-5-[(E)-2-hydroxyethoxyiminomethyl]benzamide

HRID 661715Notes

Reaction equation

[F:1][C:2]1[C:3]([NH:22][C:23]2[CH:28]=[CH:27][C:26](I)=[CH:25][C:24]=2[F:30])=[C:4]([CH:12]=[C:13]([CH:16]=[N:17][O:18][CH2:19][CH2:20][OH:21])[C:14]=1[F:15])[C:5]([NH:7][O:8][CH2:9][CH2:10][OH:11])=[O:6].C(N(CC)C(C)C)(C)C.[CH3:40][Si:41]([C:44]#[CH:45])([CH3:43])[CH3:42]>O1CCCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu](I)I>[F:1][C:2]1[C:3]([NH:22][C:23]2[CH:28]=[CH:27][C:26]([C:45]#[C:44][Si:41]([CH3:43])([CH3:42])[CH3:40])=[CH:25][C:24]=2[F:30])=[C:4]([CH:12]=[C:13](/[CH:16]=[N:17]/[O:18][CH2:19][CH2:20][OH:21])[C:14]=1[F:15])[C:5]([NH:7][O:8][CH2:9][CH2:10][OH:11])=[O:6]

Participants

Conditions

Temperature: 50 °C

Procedure

3,4-Difluoro-2-(2-fluoro-4-iodo-phenylamino)-N-(2-hydroxy-ethoxy)-5-[(2-hydroxy-ethoxyimino)-methyl]-benzamide (334 mg, 0.620 mmol) prepared in Example 1 was dissolved in anhydrous tetrahydrofuran (10 mL). (PPh3)2PdCl2 (20,867-1, Sigma-Aldrich Inc.) (21 mg, 0.031 mmol), copper iodide (11 mg, 0.0062 mmol), N,N-diisopropylethylamine (130 μL, 0.774 mmol), and trimethylsilylacetylene (1 mL) were then added thereto at room temperature. The mixture was stirred at 50° C. for two hours.

Workup

customat room temperature

Sources & evidence

ORD record: ord-43407b8912424cbdaf2364c8b87fbf11
Source dataset: uspto-grants-2011_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08084645B2

Reaction notes

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