Sodium Azide → HCID 60197896, compound

HRID 1630653Notes

Reaction equation

HRID 1630653 reaction equation
Cl[C:2]([C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)([CH3:19])[CH2:3][N:4]1[C:12]2[CH:11]=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=2[C:6]2[CH2:14][N:15]([CH3:18])[CH2:16][CH2:17][C:5]1=2.[N-:26]=[N+:27]=[N-:28].[Na+].C([O-])(O)=O.[Na+]>CN(C=O)C.O>[N:26]([C:2]([C:20]1[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=1)([CH3:19])[CH2:3][N:4]1[C:12]2[CH:11]=[CH:10][C:9]([CH3:13])=[CH:8][C:7]=2[C:6]2[CH2:14][N:15]([CH3:18])[CH2:16][CH2:17][C:5]1=2)=[N+:27]=[N-:28]

Participants

6

Reactant 3

HCID 33557Sodium AzideHCID 516892Sodium BicarbonateHCID 68284205HCID 68284205, compound

Product 1

HCID 60197896HCID 60197896, compoundYield 0.1%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
80 °C

Procedure

5-(2-Chloro-2-(pyridin-3-yl)propyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole (crude) (700 mg) was dissolved in DMF (4 mL). Sodium azide (975 mg, 15 mmol) was added and reaction mixture was stirred at 80° C. for 1 h. The reaction mixture was diluted with water, basified with aqueous NaHCO3 solution and was extracted with EtOAc (200 mL). The organic layer was washed with water (6×50 mL), dried over anhydrous sodium sulfate and evaporated in vacuo to obtain the crude product that was purified by reverse phase HPLC to obtain 1 mg of 5-(2-azido-2-(pyridin-3-yl)propyl)-2,8-dimethyl-2,3,4,5-tetrahydro-1H-pyrido[4,3-b]indole as the TFA salt. 1H NMR (CD3OD, TFA salt) δ (ppm): 8.56 (m, 2H), 8.11 (dd, 1H), 7.6 (t, 1H), 7.2 (s, 1H), 6.85 (m, 2H), 4.67 (d, 1H), 4.47 (d, 1H), 4.39 (s, 2H), 3.84 (m, 1H), 3.48 (m, 1H), 3.34 (m, 1H), 3.12 (s, 3H), 3.12 (m, 1H), 2.36 (s, 3H), 2.03 (s, 3H). Separation by chiral HPLC provides enantiomers V-3a-b.

Workup

  1. customreaction mixture
  2. extractionwas extracted with EtOAc (200 mL)
  3. washThe organic layer was washed with water (6×50 mL)
  4. dry with materialdried over anhydrous sodium sulfate
  5. customevaporated in vacuo
  6. customto obtain the crude product that
  7. customwas purified by reverse phase HPLC

Sources & evidence

ORD record
ord-95e9265d77fb45d894f5bfb7a62b41ce
Source dataset
uspto-grants-2014_07
Patent number
US08791132B2

Reaction notes

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