Potassium Phosphate, Tribasic → 6-chloro-9-(2-(3,4-dichlorophenyl)prop-1-enyl)-2-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole

6-chloro-2-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole (69 mg, 0.31 mmol) was dissolved in DMF (6 mL). To this solution was added CuI (6 mg, 0.031 mmol), L-proline (7 mg, 0.063 mmol), K3PO4 (134 mg, 0.63 mmol). The reaction mixture was stirred for 10 min at room temperature followed by addition of 4-(1-bromoprop-1-en-2-yl)-1,2-dichlorobenzene (100 mg, 0.378 mmol). The reaction mixture was heated at 80° C. overnight. Solvent was evaporated under reduced pressure; the residue was diluted with brine and extracted with ethyl acetate. Organic layer was dried over Na2SO4, and concentrated under reduced pressure. The crude product was purified by silica gel chromatography to obtain 28 mg of 6-chloro-9-(2-(3,4-dichlorophenyl)prop-1-enyl)-2-methyl-2,3,4,9-tetrahydro-1H-pyrido[3,4-b]indole. 1H NMR (DMSO) OXALATE SALT 7.95 (s, 1H), 7.62 (m, 3H), 7.30 (d, 1H), 7.20 (m, 2H), 4.30 (m, 2H), 3.40 (m, 2H), 3.0 (m, 2H), 2.82 (s, 3H), 1.90 (s, 3H).

1. temperatureThe reaction mixture was heated at 80° C. overnight
2. customSolvent was evaporated under reduced pressure
3. additionthe residue was diluted with brine
4. extractionextracted with ethyl acetate
5. dry with materialOrganic layer was dried over Na2SO4
6. concentrationconcentrated under reduced pressure
7. customThe crude product was purified by silica gel chromatography

ORD 기록

ord-6c54a86d840d471ba49c07949826fe7f

출처 데이터셋

uspto-grants-2012_12

DOI

10.6084/m9.figshare.5104873.v1

특허 번호

US08338447B2