Sulfuric Acid → 1-((1H-Pyrrolo[2,3-b]pyridin-3-yl)methyl)-6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazine

HRID 876838Notes

Reaction equation

HRID 876838 reaction equation
[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH2:10][NH:11][C:12]2[C:17]([NH2:18])=[N:16][CH:15]=[C:14]([Br:19])[N:13]=2)=[CH:2]1.[N:20]([O-])=O.[Na+].OS(O)(=O)=O.[OH-].[Na+]>CC(O)=O.O.O>[NH:1]1[C:5]2=[N:6][CH:7]=[CH:8][CH:9]=[C:4]2[C:3]([CH2:10][N:11]2[C:12]3=[N:13][C:14]([Br:19])=[CH:15][N:16]=[C:17]3[N:18]=[N:20]2)=[CH:2]1

Participants

7

Reactant 4

HCID 1118Sulfuric AcidHCID 14798Sodium HydroxideHCID 23668193Sodium NitriteHCID 86671438N2-((1H-pyrrolo[2,3-b]pyridin-3-yl)methyl)-6-bromopyrazine-2,3-diamine

Product 1

HCID 866714391-((1H-Pyrrolo[2,3-b]pyridin-3-yl)methyl)-6-bromo-1H-[1,2,3]triazolo[4,5-b]pyrazineYield 92.9%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 21899381Acetic acid--water (1/1)Solvent

Procedure

To the ice-cooled mixture of N2-((1H-pyrrolo[2,3-b]pyridin-3-yl)methyl)-6-bromopyrazine-2,3-diamine (48 mg, 0.15 mmol) in HOAc/H2O (1.5 mL/1.5 mL) was added NaNO2 (31 mg, 0.45 mmol) in water (0.2 mL). The reaction was stirred for 1.5 h in an ice bath, then aqueous H2SO4 (49%, 0.1 mL) was added. The resulting mixture was allowed to warm to room temperature and stir overnight, then was adjusted to pH>8 with 3 N aqueous NaOH solution, and extracted with EtOAc. The combined organics were dried over Na2SO4, filtered and concentrated to give the title compound (46 mg) MS (m/z): 332 (M+1)+.

Workup

  1. stirringstir overnight
  2. extractionextracted with EtOAc
  3. dry with materialThe combined organics were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated

Sources & evidence

ORD record
ord-6f924434551447368861d71238c289b8
Source dataset
uspto-grants-2015_03
Patent number
US08987269B2

Reaction notes

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