beta-Bromostyrene → (E)-2,8-dimethyl-5-styryl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole

HRID 1401475Notes

Reaction equation

[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[NH:6][C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1.Br[CH:17]=[CH:18][C:19]1[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=1.N1CCC[C@H]1C(O)=O.P([O-])([O-])([O-])=O.[K+].[K+].[K+]>CN(C=O)C.[Cu]I>[CH3:1][N:2]1[CH2:15][CH2:14][C:5]2[N:6](/[CH:17]=[CH:18]/[C:19]3[CH:24]=[CH:23][CH:22]=[CH:21][CH:20]=3)[C:7]3[CH:8]=[CH:9][C:10]([CH3:13])=[CH:11][C:12]=3[C:4]=2[CH2:3]1

Participants

Conditions

Temperature: 80 °C

Procedure

2,8-Dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (100 mg, 0.5 mmol), β-bromo styrene (91 mg, 0.55 mmol), CuI (9 mg, 0.05 mmol), L-proline (11 mg, 0.1 mmol) and potassium phosphate (212 mg, 1 mmol) taken in DMF (3 mL) under inert atmosphere, heated overnight at 80° C. The reaction mixture was cooled to RT, quenched with water, extracted with EtOAc, dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography to afford 35 mg of title compound as the free base. 1H NMR (CDCl3, HCl salt) δ (ppm): 7.60-7.55 (d, 1H), 7.50-7.45 (m, 3H), 7.42-7.38 (m, 2H), 7.25-7.20 (m, 2H), 7.15-7.10 (d, 1H), 6.80-6.75 (d, 1H), 3.75 (s, 2H), 3.12-3.05 (m, 2H), 2.98-2.90 (m, 2H), 2.67 (s, 3H), 2.50 (s, 3H).

Workup

temperatureThe reaction mixture was cooled to RT
customquenched with water
extractionextracted with EtOAc
dry with materialdried over anhydrous sodium sulfate
customevaporated under reduced pressure
customThe crude product was purified by column chromatography

Sources & evidence

ORD record: ord-f8a4e79e7461441fb35af6bfb0c42205
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907097B2

Reaction notes

Loading…