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Thionyl Chloride → 2-(1-azidobut-3-enyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazine

HRID 1969528
Notes
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Reaction equation

HRID 1969528 reaction equation
[S:1]([N:11]1[C:15]2=[N:16][CH:17]=[C:18]([CH:20](O)[CH2:21][CH:22]=[CH2:23])[N:19]=[C:14]2[CH:13]=[CH:12]1)([C:4]1[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=1)(=[O:3])=[O:2].S(Cl)(Cl)=O.C([O-])(O)=O.[Na+].[N-:34]=[N+:35]=[N-:36].[Na+]>C(Cl)Cl.CCOC(C)=O>[N:34]([CH:20]([C:18]1[N:19]=[C:14]2[CH:13]=[CH:12][N:11]([S:1]([C:4]3[CH:10]=[CH:9][C:7]([CH3:8])=[CH:6][CH:5]=3)(=[O:3])=[O:2])[C:15]2=[N:16][CH:17]=1)[CH2:21][CH:22]=[CH2:23])=[N+:35]=[N-:36]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

7

Reactant 4

HCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 516892Sodium Bicarbonate2×HCID 58557357HCID 58557357, compound

Product 1

HCID 585572372-(1-azidobut-3-enyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazineYield 101.3%

Reagents, catalysts & solvents 2

HCID 6344
Dichloromethane
Solvent
HCID 8857Ethyl AcetateSolvent2×

Procedure

To a solution of 1-(5-tosyl-5H-pyrrolo[2,3-b]pyrazin-2-yl)but-3-en-1-ol (0.14 g, 0.41 mmol) in DCM (10 mL) was added thionyl chloride (0.045 mL, 0.61 mmol). The reaction mixture was stirred for about 8 h at ambient temperature and then EtOAc and saturated aqueous NaHCO3 (10 mL each) were added. The organic layer was separated, dried over anhydrous Na2SO4, filtered and concd in vacuo. The crude chloride was dissolved in DMF (10 mL) and sodium azide (0.159 g, 2.45 mmol) was added to the reaction mixture. The reaction mixture was stirred for about 15 h at ambient temperature and then EtOAc and saturated aqueous NaHCO3 (10 mL each) were added to the reaction mixture. The organic layer was separated, concd in vacuo, and purified by chromatography on silica gel eluting with 10-60% EtOAc in heptane to provide 2-(1-azidobut-3-enyl)-5-tosyl-5H-pyrrolo[2,3-b]pyrazine (0.153 g, 87%) as an oil: LC/MS (Table 1, Method a) Rt=2.84 min; MS m/z: 369 (M+H)+.

Workup

  1. customThe organic layer was separated
  2. dry with materialdried over anhydrous Na2SO4
  3. filtrationfiltered
  4. dissolutionThe crude chloride was dissolved in DMF (10 mL)
  5. stirringThe reaction mixture was stirred for about 15 h at ambient temperature
  6. customThe organic layer was separated
  7. customconcd in vacuo, and purified by chromatography on silica gel eluting with 10-60% EtOAc in heptane

Sources & evidence

ORD record
ord-7f558fc3533640439f601258d14e8038
Source dataset
uspto-grants-2013_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08426411B2

Reaction notes

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