تفاعل #163387

معادلة التفاعل

K2CO3

dimethyldiazo-2-oxopropylphosphonat

1-methyl-1H-pyrazole-4-carbaldehyde

cyclopropanecarboxylic acid [1-(4-iodo-phenyl)-ethyl]amide

2-butylamine

→

(S)—N-(1-(4-((1-Methyl-1H-pyrazol-4-yl) ethynyl)phenyl]ethyl}cyclopropanecarboxamide

المذيبات

water

MeOH

water

ظروف التفاعل

المعالجة

1. 1
   أخرىThe reaction is quenched by the addition of water and EtOAc
2. 2
   أخرىThe organic layer is separated
3. 3
   تجفيفdried with Na2SO4
4. 4
   أخرىthe solvent is removed in vacuo
5. 5
   workup.STIRRINGThe reaction mixture is stirred at r.t. over night
6. 6
   استخلاصextracted with DCM
7. 7
   تجفيفThe organic layer is dried with Na2SO4
8. 8
   أخرىthe solvent is evaporated in vacuo
9. 9
   أخرىThe residue is purified consecutively by column chromatography (silica gel, DCM/MeOH 98:2) and HPLC (MeOH/H2O/NH3)

الإجراء التجريبي

To 100 mg (0.91 mmol) 1-methyl-1H-pyrazole-4-carbaldehyde in 1.00 mL MeOH are added 289 mg (2.09 mmol) K2CO3 and finally dropwise 349 mg (1.82 mmol) dimethyldiazo-2-oxopropylphosphonat (in 2.0 mL MeOH).The reaction mixture is stirred at r.t. over night. The reaction is quenched by the addition of water and EtOAc. The organic layer is separated, dried with Na2SO4 and the solvent is removed in vacuo. To the residue is added 286 mg (0.91 mmol) cyclopropanecarboxylic acid [1-(4-iodo-phenyl)-ethyl]amide (I52.2), 63.7 mg (0.09 mmol) bis-(triphenylphosphin)-palladiumdichlorid, 2.00 mL 2-butylamine and 2.00 mL water. The reaction mixture is stirred at r.t. over night. The mixture is diluted with water and extracted with DCM. The organic layer is dried with Na2SO4 and the solvent is evaporated in vacuo. The residue is purified consecutively by column chromatography (silica gel, DCM/MeOH 98:2) and HPLC (MeOH/H2O/NH3).

المصدر