Water → 2-(4-(azidomethyl)-1H-imidazol-1-yl)-5-bromopyridine

HRID 643007Notes

Reaction equation

HRID 643007 reaction equation
[Br:1][C:2]1[CH:3]=[CH:4][C:5]([N:8]2[CH:12]=[C:11]([CH2:13]O)[N:10]=[CH:9]2)=[N:6][CH:7]=1.O=S(Cl)Cl.[N-:19]=[N+:20]=[N-:21].[Na+].O>CC#N.CCOC(C)=O>[N:19]([CH2:13][C:11]1[N:10]=[CH:9][N:8]([C:5]2[CH:4]=[CH:3][C:2]([Br:1])=[CH:7][N:6]=2)[CH:12]=1)=[N+:20]=[N-:21]

Participants

7

Reactant 4

HCID 962WaterHCID 24386Thionyl ChlorideHCID 33557Sodium AzideHCID 68511931(1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methanol

Product 1

HCID 866140062-(4-(azidomethyl)-1H-imidazol-1-yl)-5-bromopyridineYield 87.4%

Reagents, catalysts & solvents 2

HCID 6342AcetonitrileSolventHCID 8857Ethyl AcetateSolvent

Procedure

To a suspension of (1-(5-bromopyridin-2-yl)-1H-imidazol-4-yl)methanol (520 mg, 2.05 mmol) in CH3CN (5 mL) at room temperature was added SOCl2 (2.5 mL). With the addition, the suspension became clear. After 10 min of stirring, the mixture was concentrated in vacuo. The residue was dissolved in DMF (12 mL), and NaN3 (565 mg, 8.69 mmol) was added. The mixture was stirred at room temperature overnight. H2O and EtOAc were added. The organic phase was separated, washed with 5% NaHCO3, dried over Na2SO4, concentrated in vacuo to give 2-(4-(azidomethyl)-1H-imidazol-1-yl)-5-bromopyridine (500 mg).

Workup

  1. additionWith the addition
  2. concentrationthe mixture was concentrated in vacuo
  3. dissolutionThe residue was dissolved in DMF (12 mL)
  4. stirringThe mixture was stirred at room temperature overnight
  5. customThe organic phase was separated
  6. washwashed with 5% NaHCO3
  7. dry with materialdried over Na2SO4
  8. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-29979b9fd74c48948f8607ff06295fb7
Source dataset
uspto-grants-2010_04
Patent number
US07696352B2

Reaction notes

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