Sodium Azide → 5-(Azidomethyl)isoquinoline

HRID 1861674Notes

Reaction equation

HRID 1861674 reaction equation
Cl[CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]=[CH:8]2.[N-:13]=[N+:14]=[N-:15].[Na+]>CN(C=O)C.CCOC(C)=O>[N:13]([CH2:2][C:3]1[CH:12]=[CH:11][CH:10]=[C:9]2[C:4]=1[CH:5]=[CH:6][N:7]=[CH:8]2)=[N+:14]=[N-:15]

Participants

5

Reactant 2

HCID 33557Sodium Azide2×HCID 120186945-(Chloromethyl)isoquinoline

Product 1

HCID 120186955-(Azidomethyl)isoquinoline

Reagents, catalysts & solvents 2

HCID 6228DimethylformamideSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a solution of 0.0415 g (0.23 mmol) 16 in 3 mL DMF was added 0.0169 g (0.26 mmol) sodium azide. After a 3 h, an additional 0.0033g (0.05 mmol) portion of sodium azide was added. After 24 h at room temperature, the reaction mixture was diluted with 50 mL EtOAc and washed with 20 mL brine. The aqueous layer was extracted with 10 mL EtOAc. The combined organic layers were dried over Na2SO4, filtered and concentrated in vacuo. Purification by flash chromatography (10×175 mm silica gel, linear gradient 5-20% EtOAc:hexane) produced 17. 1H NMR (CDCl3, 400 MHz) δ 9.318 (s, 1H, ArH); 8.637 (d, 1H, J=6.10 Hz, ArH); 8.010 (d, 1H, J=7.94 Hz, ArH); 7.822 (d, 1H, J=6.10 Hz, ArH); 7.713 (d, 1H, J=7.02 Hz, ArH); 7.617 (dd, 1H, J=7.17, 8.09 Hz, ArH); 4.774 (s, 1H, ArH); MS (Electrospray): m/z 185.0 (M+H).

Workup

  1. waitAfter 24 h at room temperature
  2. washwashed with 20 mL brine
  3. extractionThe aqueous layer was extracted with 10 mL EtOAc
  4. dry with materialThe combined organic layers were dried over Na2SO4
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customPurification by flash chromatography (10×175 mm silica gel, linear gradient 5-20% EtOAc:hexane)

Sources & evidence

ORD record
ord-8532594578b346208285051fece14f70
Source dataset
uspto-grants-2003_03
Patent number
US06534510B2

Reaction notes

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