Triethylamine → HCID 178441282, compound

HRID 76265Notes

Reaction equation

[CH2:1]([C:5]1=[CH:6][N:7]([C:22]([CH3:25])([CH3:24])[CH3:23])[S:8]/[C:9]/1=[N:10]\[C:11](=[O:21])[C:12]1[CH:17]=[C:16](I)[CH:15]=[CH:14][C:13]=1[O:19][CH3:20])[CH2:2][CH2:3][CH3:4].[C:26]([Si:28]([CH3:31])([CH3:30])[CH3:29])#[CH:27].C(N(CC)CC)C>CN(C=O)C.O.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>[CH2:1]([C:5]1=[CH:6][N:7]([C:22]([CH3:25])([CH3:24])[CH3:23])[S:8]/[C:9]/1=[N:10]\[C:11](=[O:21])[C:12]1[CH:17]=[C:16]([C:27]#[C:26][Si:28]([CH3:31])([CH3:30])[CH3:29])[CH:15]=[CH:14][C:13]=1[O:19][CH3:20])[CH2:2][CH2:3][CH3:4]

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of the product from Example 61 (330 mg, 0.7 mmol), ethynyltrimethylsilane (206 mg, 2.1 mmol), PdCl2(PPh3)2 (49 mg, 0.07 mmol), triethylamine (201 mg, 2.1 mmol) and CuI (33 mg, 0.18 mmol) in DMF (5 mL) was heated at 50° C. for 16 hrs, diluted with H2O and extracted with EtOAc (2×). The organic layer was dried over MgSO4, filtered and concentrated. The residue was purified by column chromatography using an Analogix® Intelliflash280™ (SiO2, 0-50% Hexane in ethyl acetate) to afford 300 mg (97%) of the title compound. MS (DCI/NH4+) m/z 443 (M+H)+.

Workup

extractionextracted with EtOAc (2×)
dry with materialThe organic layer was dried over MgSO4
filtrationfiltered
concentrationconcentrated
customThe residue was purified by column chromatography

Sources & evidence

ORD record: ord-44606d70d3b74ce8a202d5e72cf21824
Source dataset: uspto-grants-2014_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08835475B2

Reaction notes

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