تفاعل #91810

معادلة التفاعل

Triphenylphosphine

Compound ( 1 )

2-(4-Chlorophenyl)-5-cyclopropyl-N-methyl-6-[(methylsulfonyl)amino]-2H-indazole-3-carboxamide

5-cyclopropyl-2,4-dinitrobenzaldehyde

5-methylpyridin-2-amine

→

( ii )

المردود 43.0%

5-Cyclopropyl-2-(5-methylpyridin-2-yl)-6-nitro-2H-indazole

المردود 43.0%

المذيبات

EtOH

DCM

ظروف التفاعل

المعالجة

1. 1
   أخرىhad precipitated from solution
2. 2
   أخرىthe reaction
3. 3
   درجة الحرارةUpon cooling to RT
4. 4
   غسيلthe organics were washed with aq. 30% hydrogen peroxide solution (2 mL)
5. 5
   أخرىThe organics were separated
6. 6
   ترشيحfiltered through a plug of MgSO4
7. 7
   أخرىpurified by automated column chromatography (Biotage SP4, Grace 4 g silica cartridge)
8. 8
   غسيلeluting with EtOAc

الإجراء التجريبي

To a stirred solution of 5-cyclopropyl-2,4-dinitrobenzaldehyde (prepared according to the synthesis of Compound (1)) (50 mg, 0.212 mmol) in EtOH (750 mL) was added 5-methylpyridin-2-amine (25 mg, 0.23 mmol) and the resultant solution stirred at RT for 2d after which time a solid had precipitated from solution. Triphenylphosphine (167 mg, 0.64 mmol) was added in a single portion and the reaction then heated at 100° C. in a sealed tube for 4 h. Upon cooling to RT, the reaction was diluted with DCM (2 mL) and the organics were washed with aq. 30% hydrogen peroxide solution (2 mL). The organics were separated and filtered through a plug of MgSO4 and then purified by automated column chromatography (Biotage SP4, Grace 4 g silica cartridge) eluting with EtOAc:n-heptane (gradient elution, 0% equil. (2 CV), 0% (1CV), 0 to 100% (35 CV), 100% (5 CV)) to give (ii) (27 mg, 43%). ESI-MS: calculated [M+H]+ 295.1. observed [M+H]+ 295.2.

المصدر