تفاعل #966560

معادلة التفاعل

(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(2-(trifluoromethylsulfonyloxy)quinolin-6-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetate

cyclohexanecarboxamide

Xantphos

Cs2CO3

→

desired product

(S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-2-(2-(2-(cyclohexanecarboxamido)quinolin-6-yl)pyridin-4-yl)-5-methylbenzo[d]thiazol-6-yl)acetate

المذيبات

dioxane

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction was degassed for 5 minutes with N2
2. 2
   درجة الحرارةAfter cooling
3. 3
   workup.ADDITIONthe reaction mixture was diluted with EtOAc
4. 4
   استخلاصextracted with H2O, brine
5. 5
   تجفيفdried over Na2SO4
6. 6
   ترشيحfiltered
7. 7
   تركيزconcentrated
8. 8
   أخرىpurified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes)

الإجراء التجريبي

To a solution of (S)-ethyl 2-tert-butoxy-2-(7-(4-chlorophenyl)-5-methyl-2-(2-(2-(trifluoromethylsulfonyloxy)quinolin-6-yl)pyridin-4-yl)benzo[d]thiazol-6-yl)acetate (28.4 mg, 0.037 mmol) in anhydrous dioxane (0.6 mL) was added cyclohexanecarboxamide (7.0 mg, 0.055 mmol), Xantphos (2.0 mg, 0.004 mmol), Cs2CO3 (36.0 mg, 0.111 mmol) and Pd2(dba)3 (2.0 mg, 0.002 mmol). The reaction was degassed for 5 minutes with N2 and then heated at 100° C. for 2 h. After cooling, the reaction mixture was diluted with EtOAc, extracted with H2O, brine, dried over Na2SO4, filtered and concentrated and purified by flash column chromatography (silica gel, 0 to 100% ethyl acetate/hexanes) to give the desired product. LCMS-ESI+ (m/z): [M+H]+ calcd for C43H44ClN4O4S: 747.3; found: 747.2.

المصدر