Cyclobutylamine → HCID 59455252, compound

HRID 1400587Notes

Reaction equation

HRID 1400587 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+].[CH:31]1([NH2:35])[CH2:34][CH2:33][CH2:32]1>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[CH:31]1([NH:35][C:2]2[CH:10]=[CH:9][C:8]3[N:7](/[CH:11]=[C:12](/[C:14]4[CH:19]=[CH:18][N:17]=[CH:16][CH:15]=4)\[CH3:13])[C:6]4[CH2:20][CH2:21][N:22]([CH3:24])[CH2:23][C:5]=4[C:4]=3[CH:3]=2)[CH2:34][CH2:33][CH2:32]1

Participants

5

Reactant 3

HCID 75645CyclobutylamineHCID 23676156Sodium t-butoxideHCID 67309592HCID 67309592, compound

Product 1

HCID 59455252HCID 59455252, compoundYield 37.3%

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, cyclobutylamine (24.3 mg, 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 34 mg of desired compound as the TFA salt. 1H NMR (CD3OD, TFA salt) δ (ppm): 8.80 (d, 2H), 8.10 (d, 2H), 7.62 (d, 2H), 7.44 (d, 1H), 7.30 (d, 1H), 4.50 (m, 2H), 4.18 (m, 1H), 3.85 (m, 1H), 3.70 (m, 1H), 3.26 (m, 2H), 3.18 (s, 3H), 2.38 (m, 4H), 2.10 (s, 3H), 2.02-1.85 (m, 2H).

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-2d0015db464e48ff91029609e43febd7
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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