Trimethylsilylacetylene → HCID 23132351, compound

HRID 661719Notes

Reaction equation

HRID 661719 reaction equation
[F:1][C:2]1[C:3]([NH:24][C:25]2[CH:30]=[CH:29][C:28](I)=[CH:27][C:26]=2[F:32])=[C:4]([CH:12]=[C:13]([CH:16]=[N:17][O:18][CH2:19][C:20]([OH:23])([CH3:22])[CH3:21])[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.[CH3:42][Si:43]([C:46]#[CH:47])([CH3:45])[CH3:44]>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:24][C:25]2[CH:30]=[CH:29][C:28]([C:47]#[C:46][Si:43]([CH3:45])([CH3:44])[CH3:42])=[CH:27][C:26]=2[F:32])=[C:4]([CH:12]=[C:13](/[CH:16]=[N:17]/[O:18][CH2:19][C:20]([OH:23])([CH3:22])[CH3:21])[C:14]=1[F:15])[C:5]([NH:7][O:8][CH2:9][CH2:10][OH:11])=[O:6]

Participants

7

Reactant 3

HCID 66111TrimethylsilylacetyleneHCID 81531DiisopropylethylamineHCID 72827292HCID 72827292, compound

Product 1

HCID 23132351HCID 23132351, compound

Reagents, catalysts & solvents 3

HCID 83717Copper iodideCatalystHCID 178418476HCID 178418476, compoundCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

3,4-Difluoro-2-(2-fluoro-4-iodophenylamino)-N-(2-hydroxy-ethoxy)-5-[(2-hydroxy-2-methyl-propoxyimino)-methyl]-benzamide (14.6 mg, 0.025 mmol) prepared in Example 12 was dissolved in anhydrous tetrahydrofuran (2.0 ml). Next, (PPh3)2PdCl2 (20,867-1, Sigma-Aldrich, Inc.) (1.0 mg, 0.00127 mmol), copper iodide (2.0 mg, 0.0094 mmol), N,N-diisopropylethylamine (10 μL, 0.057 mmol), and trimethylsilylacetylene (35 μL, 0.25 mmol) were added thereto at room temperature, and the mixture was stirred at 50° C. overnight.

Sources & evidence

ORD record
ord-34fa8a9a8bd94514b160fbb21bd5eb0c
Source dataset
uspto-grants-2011_12
Patent number
US08084645B2

Reaction notes

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