Butylamine → HCID 59454916, compound

HRID 1401654Notes

Reaction equation

HRID 1401654 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+].[CH2:31]([NH2:35])[CH2:32][CH2:33][CH3:34]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH2:31]([NH:35][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)[CH2:32][CH2:33][CH3:34]

Participants

5

Reactant 3

HCID 8007ButylamineHCID 23676156Sodium t-butoxideHCID 67309592HCID 67309592, compound

Product 1

HCID 59454916HCID 59454916, compoundYield 99.2%

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 were evacuated and back filled with nitrogen for 5 min. Dry toluene (2 mL) was added under nitrogen atmosphere. Finally, N-butyl amine (0.034 mL, 0.343 mmol) was added to the reaction mixture and contents heated at 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 91 mg of desired compound as the TFA salt. 1H NMR (CD3OD, TFA salt) δ (ppm): 8.82 (d, 2H), 8.24 (d, 2H), 7.74 (d, 2H), 7.50 (d, 1H), 7.38 (d, 1H), 4.50 (m, 2H), 3.90 (m, 1H), 3.70 (m, 1H), 3.42 (m, 2H), 3.26 (m, 2H), 3.18 (s, 3H), 2.10 (s, 3H), 1.76 (m, 2H), 1.46 (m, 2H), 1.0 (t, 3H).

Workup

  1. customwere 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-0b53a11dbea64851adbff38834bd14e2
Source dataset
uspto-grants-2014_12
Patent number
US08907097B2

Reaction notes

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