تفاعل #1751680

معادلة التفاعل

KH2PO4

(±)-6-cyano-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid methyl-phenyl-amide

KOtBu

ethyl bromoacetate

→

subtitle compound

المردود 51.0%

Ethyl (±)-[6-cyano-3-(methyl-phenyl-carbamoyl)-1,2,3,4-tetrahydro-carbazol-9-yl]-acetate

المردود 51.0%

المذيبات

DMF

ظروف التفاعل

المعالجة

1. 1
   استخلاصextracted with CH2Cl2
2. 2
   غسيلThe combined organic layers are washed with H2O and brine
3. 3
   تجفيفdried over Na2SO4
4. 4
   ترشيحfiltered
5. 5
   أخرىevaporated
6. 6
   أخرىThe residue is purified by column chromatography on silica gel (hexane/EtOAc 1:1)

الإجراء التجريبي

To a stirred solution of (±)-6-cyano-2,3,4,9-tetrahydro-1H-carbazole-3-carboxylic acid methyl-phenyl-amide (0.14 g, 0.43 mmol) in dry DMF (1.5 ml) is added KOtBu (58 mg, 0.52 mmol) and ethyl bromoacetate (79 mg, 0.47 mmol). The reaction mixture is stirred at rt overnight, then poured into saturated aqueous KH2PO4 and extracted with CH2Cl2. The combined organic layers are washed with H2O and brine, dried over Na2SO4, filtered and evaporated. The residue is purified by column chromatography on silica gel (hexane/EtOAc 1:1) to provide subtitle compound (91 mg) as a beige solid in 51% yield. tR (LC-3) 1.15 min; ESI-MS (positive ion): m/z 416.09 [M+H]+ (calcd 415.19 for C25H25N3O3). 1H-NMR (CDCl3): 1.13 (t, J=7.0 Hz, 3H); 1.79 (m, 1H); 2.05 (m, 1H); 2.25 (m, 1H); 2.65 (m, 1H); 2.72 (m, 2H); 3.19 (s, 3H); 3.24 (m, 1H); 4.07 (q, J=7.0 Hz, 2H); 5.00 (d, J=3.3 Hz, 2H); 7.33 (m, 1H); 7.41 (m, 5H); 7.50 (d, J=8.0 Hz, 1H); 7.87 (s, 1H).

المصدر