Pyrrolidine → HCID 59455129, compound

HRID 1401655Notes

Reaction equation

HRID 1401655 reaction equation
Cl[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]([CH3:24])[CH2:23][C:5]=3[C:4]=2[CH:3]=1.CC(C)([O-])C.[Na+].[NH:31]1[CH2:35][CH2:34][CH2:33][CH2:32]1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH3:24][N:22]1[CH2:21][CH2:20][C:6]2[N:7](/[CH:11]=[C:12](/[C:14]3[CH:15]=[CH:16][N:17]=[CH:18][CH:19]=3)\[CH3:13])[C:8]3[CH:9]=[CH:10][C:2]([N:31]4[CH2:35][CH2:34][CH2:33][CH2:32]4)=[CH:3][C:4]=3[C:5]=2[CH2:23]1

Participants

5

Reactant 3

HCID 31268PyrrolidineHCID 23676156Sodium t-butoxideHCID 67309592HCID 67309592, compound

Product 1

HCID 59455129HCID 59455129, compoundYield 27.4%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
100 °C

Procedure

8-Chloro-2-methyl-5-(2-pyridin-4-yl-propenyl)-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (0.100 g, 0.245 mmol), sodium tertbutoxide (0.283 g, 2.948 mmol), palladium acetate (0.010 g, 0.049 mmol) and 2-di-tertbutylphosphino-2′-4′-6′-triisopropylbiphenyl (0.031 g, 0.0735 mmol) were charged in a reaction bottle which was evacuated and back filled with nitrogen for 5 min. Dry toluene (2 mL) was added under nitrogen atmosphere. Finally, pyrrolidine (0.033 mL, 0.343 mmol) was added to the reaction mixture and the contents heated to 100° C. overnight. The reaction mixture was filtered and precipitate washed with EtOAc (2×25 mL). The filtrate was concentrated under vacuum and purified by reverse phase chromatography to yield 25 mg of desired compound as the TFA salt. 1H NMR (CD3OD, TFA salt) δ (ppm): 8.78 (d, 2H), 8.18 (d, 2H), 7.68 (s, 1H), 7.50 (s, 1H), 7.39 (d, 1H), 7.24 (d, 1H), 4.78 (m, 1H), 4.45 (m, 1H), 3.90 (m, 1H), 3.74-3.60 (m, 5H), 3.24 (m, 2H), 3.18 (s, 3H), 2.24 (m, 4H), 2.10 (s, 3H).

Workup

  1. customwas evacuated
  2. additionback filled with nitrogen for 5 min
  3. additionDry toluene (2 mL) was added under nitrogen atmosphere
  4. filtrationThe reaction mixture was filtered
  5. washprecipitate washed with EtOAc (2×25 mL)
  6. concentrationThe filtrate was concentrated under vacuum
  7. custompurified by reverse phase chromatography

Sources & evidence

ORD record
ord-7cc9601ca6fd4a59b51b67911a73310e
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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