Dimethylamine, hydrochloride → HCID 59455265, compound

HRID 1400582Notes

Reaction equation

HRID 1400582 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][C:17]([F:20])=[CH:16][CH:15]=3)[CH3:13])[C:6]3[CH2:21][CH2:22][N:23]([CH3:25])[CH2:24][C:5]=3[C:4]=2[CH:3]=1.CC(C)([O-])C.[Na+].Cl.[CH3:33][NH:34][CH3:35]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[F:20][C:17]1[CH:18]=[CH:19][C:14](/[C:12](/[CH3:13])=[CH:11]/[N:7]2[C:8]3[CH:9]=[CH:10][C:2]([N:34]([CH3:35])[CH3:33])=[CH:3][C:4]=3[C:5]3[CH2:24][N:23]([CH3:25])[CH2:22][CH2:21][C:6]2=3)=[CH:15][CH:16]=1

Participants

5

Reactant 3

HCID 10473Dimethylamine, hydrochlorideHCID 23676156Sodium t-butoxideHCID 67309559HCID 67309559, compound

Product 1

HCID 59455265HCID 59455265, compoundYield 33.2%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Conditions

Temperature
100 °C

Procedure

8-Chloro-5-(2-(4-fluorophenyl)prop-1-enyl)-2,3,4,5-tetrahydro-2-methyl-1H-pyrido[4,3-b]indole (100 mg, 0.282 mmol), sodium tertbutoxide (324 mg, 2.948 mmol), palladium acetate (12 mg, 0.049 mmol) and 2-di-tertbutylphosphino-2′-4′-6′-triisopropylbiphenyl (31 mg, 0.0735 mmol) were charged in a reaction bottle which was evacuated and back filled with nitrogen for 5 min. Anhydrous toluene (2 mL) was added under nitrogen atmosphere. Finally, dimethylamine hydrochloride (45.13 mg, 0.564 mmol) was added to the reaction mixture and contents heated at 100° C. overnight. The reaction mixture was filtered, and washed with EtOAc (2×25 mL). The filtrate obtained was concentrated under vacuum and purified on reverse phase chromatography to yield 34 mg of desired compound as the TFA salt. 1H NMR (CD3OD, TFA salt) δ (ppm): 7.78 (s, 1H), 7.58 (m, 2H), 7.38 (s, 2H), 7.10 (t, 2H), 6.90 (s, 1H), 4.70 (m, 1H), 4.40 (m, 1H), 3.80 (m, 1H), 3.58 (m, 1H), 3.28 (s, 6H), 3.10 (m, 2H), 3.05 (s, 3H), 1.80 (s, 3H).

Workup

  1. customwas evacuated
  2. additionback filled with nitrogen for 5 min
  3. additionAnhydrous toluene (2 mL) was added under nitrogen atmosphere
  4. filtrationThe reaction mixture was filtered
  5. washwashed with EtOAc (2×25 mL)
  6. customThe filtrate obtained
  7. concentrationwas concentrated under vacuum
  8. custompurified on reverse phase chromatography

Sources & evidence

ORD record
ord-1889ce4b136a46d4a2d3f9637b1e9bb2
Source dataset
uspto-grants-2014_12
Patent number
US08906925B2

Reaction notes

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