Phenethyl bromide → HCID 67309784, compound

HRID 1401626Notes

Reaction equation

HRID 1401626 reaction equation
[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[CH3:13])[C:6]3[CH2:20][CH2:21][NH:22][CH2:23][C:5]=3[C:4]=2[CH:3]=1.Br[CH2:25][CH2:26][C:27]1[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=1>C(#N)C.C(=O)(O)[O-]>[CH3:1][C:2]1[CH:10]=[CH:9][C:8]2[N:7]([CH:11]=[C:12]([C:14]3[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=3)[CH3:13])[C:6]3[CH2:20][CH2:21][N:22]([CH2:25][CH2:26][C:27]4[CH:32]=[CH:31][CH:30]=[CH:29][CH:28]=4)[CH2:23][C:5]=3[C:4]=2[CH:3]=1

Participants

5

Reactant 2

HCID 7666Phenethyl bromideHCID 67310663HCID 67310663, compound

Product 1

HCID 67309784HCID 67309784, compoundYield 6.5%

Reagents, catalysts & solvents 2

HCID 769Bicarbonate IonSolventHCID 6342AcetonitrileSolvent

Conditions

Temperature
80 °C

Procedure

8-Methyl-5-(2-pyridin-4-yl-propenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (100 mg, 0.33 mmol) was dissolved in acetonitrile (1 mL) and (2-Bromo-ethyl)-benzene (62 mg, 0.33 mmol) was added to the reaction mixture. The contents were heated to 80° C. for 2 h. The reaction mixture was cooled to RT after 2 h and diluted with saturated bicarbonate (20 mL). The desired compound was extracted with EtOAc (2×50 mL). The organic layer dried over sodium sulfate and concentrated under vacuum to obtain the crude product which was purified by reverse phase chromatography to obtain 8.7 mg of 8-Methyl-2-phenethyl-5-(2-pyridin-4-yl-propenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole. 1H NMR (CDCl3, TFA salt) δ (ppm): 8.82 (d, 2H), 7.90 (d, 2H), 7.42 (s, 1H), 7.38-7.22 (m, 6H) 7.16 (d, 1H), 7.02 (d, 1H), 4.90 (m, 1H), 4.20 (m, 1H), 3.98 (m, 1H), 3.60-3.40 (m, 4H), 3.24 (m, 2H), 2.95 (m, 1H), 2.44 (s, 3H), 2.12 (s, 3H).

Workup

  1. temperatureThe reaction mixture was cooled to RT after 2 h
  2. extractionThe desired compound was extracted with EtOAc (2×50 mL)
  3. dry with materialThe organic layer dried over sodium sulfate
  4. concentrationconcentrated under vacuum
  5. customto obtain the crude product which
  6. customwas purified by reverse phase chromatography

Sources & evidence

ORD record
ord-022305e48852437db19fda61293c931f
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

Loading…