HCID 178492730, compound → HCID 178492730, compound

Temperature

80 °C

Other

Reaction stirred at 80 degrees Celcius for 24 hours, then cooled to room temperature and opened to air before adding the internal standard.

Vials containing pre-plated ligand were added to a 96-well reaction block (Paradox Standard 96-Position Parallel Synthesis block) in positions C4-9 ,D4-9, E4-9, and F4-9 and equipped with magnetic stirbars in a moisture and oxygen-free glovebox. The remainder of the plate positions were filled with empty vials to ensure a proper seal with the lid could be obtained later.(cod)Pd(CH2TMS)2 (0.13 mg, 0.33 umol, 0.10 equiv) and nBu3N (4.10 uL, 16.7 umol, 5.00 equiv) were added as a solution in MeCN (150 uL) via micropipettor to each of the 24 wells. Then hydroxamic ether 3 (1.49 mg, 3.34 umol, 1.00 equiv) was added as a solution in MeCN (150 uL) via micropipettor. The reaction block was then covered with a Teflon sheet, rubber mats, and its aluminum top cover which were all affixed to the bottom plate via 9 tightly tightened screws. The plate was placed in a pre-heated temperature-controlled metal block on a stir plate in the glovebox and stirred at 80C for 24 h. The reaction block was then removed from the glovebox, cooled to rt, and opened to air. A solution of trimethoxybenzene (0.19 mg, 1.11 umol, 0.33 equiv) in MeCN (400 uL) was added as an internal standard to each vial of the 24 vials via micropipettor. After centrifugation, a 300 uL aliquot of each crude reaction was transferred to an analysis collection plate via micropipettor. The plate was sealed with aluminum sealing tape, and centrifuged for 15 min. The reactions were analyzed and quantified by LC-MS and integrated against the trimethoxybenzene internal standard to determine the yield of product formed in each reaction and the amount of unreacted starting material remaining. Yields determined by LC-MS were also validated by quantification of the 1H NMR spectrum of the indicated entries.

1. temperaturecool to room temperature and opened to air
2. additionaddition of internal standard
3. aliquot300 microliter aliquot transferred to analysis collection plate via micropipettor, and sealed with aluminium sealing tape.
4. customcentrifuged · Keep liquid

ORD record

ord-79c5efba46be4f06ab681b9ff9454bda

Source dataset

Ligand screening for Aza-Heck cyclization in total synthesis of Impatien A

DOI

10.1021/acs.orglett.1c02767

Original link

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