Water → HCID 59454908, compound

HRID 1400553Notes

Reaction equation

I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[CH3:8][N:9]1[CH2:25][CH2:24][C:12]2[N:13]([CH:21]=[CH:22][CH3:23])[C:14]3[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][C:19]=3[C:11]=2[CH2:10]1.O>N(CCO)(CCO)CCO.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:8][N:9]1[CH2:25][CH2:24][C:12]2[N:13](/[C:21](/[C:2]3[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=3)=[CH:22]\[CH3:23])[C:14]3[CH:15]=[CH:16][C:17]([CH3:20])=[CH:18][C:19]=3[C:11]=2[CH2:10]1

Participants

Conditions

Temperature: 100 °C

Procedure

Iodo benzene (0.5 g, 2.4 mmol) and 2,8-dimethyl-5-(prop-1-enyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (588 mg, 2.4 mmol) were charged in triethanolamine (4 mL). Palladium (II)acetate (5 mg, 0.024 mmol) was added and stirred at 100° C. for 14 h. The reaction was monitored by TLC and LCMS. After completion of the reaction, water was added. The desired compound was extracted with diethyl ether twice. The organic layer was dried over anhydrous sodium sulfate and evaporated under reduced pressure. The crude product was purified by column chromatography to afford 0.3 g of product. 1H NMR (CD3OD, TFA salt) δ (ppm): 7.24 (s, 1H), 7.18 (m, 3H), 6.96-6.82 (m, 4H), 6.62 (m, 1H), 4.66 (m, 1H), 4.30 (m, 1H), 3.64 (m, 1H), 3.42 (m, 1H), 3.0 (s, 1H), 2.80 (m, 1H), 2.60 (m, 1H), 2.36 (s, 3H), 1.50 (d, 3H).

Workup

additionwas added
extractionThe desired compound was extracted with diethyl ether twice
dry with materialThe organic layer was dried over anhydrous sodium sulfate
customevaporated under reduced pressure
customThe crude product was purified by column chromatography

Sources & evidence

ORD record: ord-30dac5a10afb4547ac79931359e02a4e
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08906925B2

Reaction notes

Loading…