Water → HCID 59454908, compound

HRID 1401622Notes

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-3d504017f1644fcbaa5e38c5ea3fcd55
Source dataset: uspto-grants-2014_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08907097B2

Reaction notes

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