Sodium Nitrite → 6-bromo-1-(2,3-dihydro-benzofuran-5-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine

HRID 15991

Reaction equation

HRID 15991 reaction equation
[Br:1][C:2]1[N:7]=[C:6]([NH:8][CH2:9][C:10]2[CH:11]=[CH:12][C:13]3[O:17][CH2:16][CH2:15][C:14]=3[CH:18]=2)[C:5]([NH2:19])=[N:4][CH:3]=1.[N:20]([O-])=O.[Na+]>CC(O)=O.O>[Br:1][C:2]1[N:7]=[C:6]2[N:8]([CH2:9][C:10]3[CH:11]=[CH:12][C:13]4[O:17][CH2:16][CH2:15][C:14]=4[CH:18]=3)[N:20]=[N:19][C:5]2=[N:4][CH:3]=1

Participants

5

Reactant 2

HCID 23668193Sodium NitriteHCID 593418606-bromo-N2-(2,3-dihydro-benzofuran-5-ylmethyl)-pyrazine-2,3-diamine

Product 1

HCID 593418446-bromo-1-(2,3-dihydro-benzofuran-5-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazineYield 52.4%

Reagents, catalysts & solvents 2

HCID 176Acetic AcidSolventHCID 962WaterSolvent2×

Procedure

To a solution of 6-bromo-N2-(2,3-dihydro-benzofuran-5-ylmethyl)-pyrazine-2,3-diamine (1.0 g, 3.12 mmol) in AcOH:H2O (8 mL: 8 mL) was added the solution of NaNO2 (2.12 g, 31.2 mmol) in water (5 mL). The mixture was stirred at room temperature for 1 hour, and then heated at 65° C. for 16 hours. The solvents were removed, and then EtOAc (20 mL) and water (20 mL) were added. The aqueous layer was extracted with EtOAc (3×20 mL). The combined extracts were dried over Na2SO4, concentrated and purified by silica gel chromatography with EtOAc: Hexanes to provide 6-bromo-1-(2,3-dihydro-benzofuran-5-ylmethyl)-1H-[1,2,3]triazolo[4,5-b]pyrazine (543 mg, 52% yield).

Workup

  1. temperatureheated at 65° C. for 16 hours
  2. customThe solvents were removed
  3. additionEtOAc (20 mL) and water (20 mL) were added
  4. extractionThe aqueous layer was extracted with EtOAc (3×20 mL)
  5. dry with materialThe combined extracts were dried over Na2SO4
  6. concentrationconcentrated
  7. custompurified by silica gel chromatography with EtOAc

Sources & evidence

ORD record
ord-360d4cf41c634868a6a397e84190bdae
Source dataset
uspto-grants-2010_06
Patent number
US07732604B2

Linked notes

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