Реакция #90110

ord-4b791329a9fb43fb82e8ce65ca37928e

Уравнение реакции

C1COCCO1
dioxane
CC(C)c1cc(C(C)C)c(-c2ccccc2P(C(C)(C)C)C(C)(C)C)c(C(C)C)c1
2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl
[K+].[OH-]
KOH
CC1(C)OC[C@H](COc2cc3c(cc2Br)C(=O)c2c([nH]c4cc(Cl)ccc24)C3(C)C)O1
9-Bromo-3-chloro-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one
CC1(C)OC[C@H](COc2cc3c(cc2O)C(=O)c2c([nH]c4cc(Cl)ccc24)C3(C)C)O1
title compound
CC1(C)OC[C@H](COc2cc3c(cc2O)C(=O)c2c([nH]c4cc(Cl)ccc24)C3(C)C)O1
9-Hydroxy-3-chloro-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one

Растворители

Условия реакции

Температура
60°CELSIUS
Подробные условия
See reaction.notes.procedure_details.

Обработка

  1. 1
    ТемператураAfter cooling
  2. 2
    Концентрированиеthe reaction solution was concentrated under reduced pressure
  3. 3
    Другоеthe resulting residues were purified by HPLC

Методика

9-Bromo-3-chloro-8-((S)-2,2-dimethyl-[1,3]dioxolan-4-ylmethoxy)-6,6-dimethyl-5,6-dihydro-benzo[b]carbazol-11-one (Compound S7-1, 30 mg, 0.06 mmol) was dissolved in the mixture solvent of water.dioxane (1:1) (0.5 mL), added with tris(benzylidenacetone dipalladium)chloroform complex (3.1 mg, 0.05 eq.), 2-di-tert-butylphosphino-2′,4′,6′-triisopropylbiphenyl (2.5 mg, 0.1 eq.) and KOH (0.5 N aqueous solution 180 μL, 1.5 eq.), and stirred at 60° C. for 12 hr. After cooling, the reaction solution was concentrated under reduced pressure, and the resulting residues were purified by HPLC to obtain the title compound (white solid, 4.6 mg).

Источник

DOI: 10.6084/m9.figshare.5104873.v1Патент: US09440922B2uspto-grants-2016_09