تفاعل #68614

معادلة التفاعل

6-((6-chloro-8-fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)-3-methoxyquinoline

1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole

Na2CO3

H2O

→

powder

المردود 27.4%

6-((8-fluoro-6-(1-methyl-1H-pyrazol-4-yl)-[1,2,4]-triazolo[4,3-a]pyridin-3-yl)methyl)quinolin-3-ol

المردود 27.4%

المذيبات

DMSO

DME

ظروف التفاعل

المعالجة

1. 1
   ترشيحfiltered
2. 2
   أخرىThe DMSO solution was purified on HPLC (10-60%/10 min)
3. 3
   تركيزThe product fraction was concentrated to dryness with toluene
4. 4
   أخرىThe solid was then triturated with MeOH-hexane (1:2)

الإجراء التجريبي

A mixture of crude 6-((6-chloro-8-fluoro-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methyl)-3-methoxyquinoline (200 mg, 584 μmol), 1-methyl-4-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)-1H-pyrazole (600 mg, 2884 μmol), PdCl2(dppf)-CH2Cl2 adduct (24 mg, 29 μmol), and Na2CO3 (500 mg, 4717 μmol) in DME (7 mL)-H2O (5 mL) was heated at 100° C. under nitrogen. After overnight, the sludge was treated with DMSO (10 mL) and filtered. The DMSO solution was purified on HPLC (10-60%/10 min). The product fraction was concentrated to dryness with toluene. The solid was then triturated with MeOH-hexane (1:2) to give a brown powder (60 mg). LCMS (ESI pos. ion): calc'd for C20H15FN6O: 374.1. found 375.1 (M+1).

المصدر