تفاعل #90110

ord-4b791329a9fb43fb82e8ce65ca37928e

معادلة التفاعل

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

المذيبات

ظروف التفاعل

درجة الحرارة
60°CELSIUS
الظروف التفصيلية
See reaction.notes.procedure_details.

المعالجة

  1. 1
    درجة الحرارةAfter cooling
  2. 2
    تركيزthe reaction solution was concentrated under reduced pressure
  3. 3
    أخرىthe resulting residues were purified by HPLC

الإجراء التجريبي

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).

المصدر

DOI: 10.6084/m9.figshare.5104873.v1براءة الاختراع: US09440922B2uspto-grants-2016_09