Hydrogen Bromide → 4-((6-(3-Methylisoxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)quinolin-7-ol hydrobromide

HRID 219220Notes

Reaction equation

HRID 219220 reaction equation
C[O:2][C:3]1[CH:12]=[C:11]2[C:6]([C:7]([O:13][CH2:14][C:15]3[N:19]4[CH:20]=[C:21]([C:24]5[O:28][N:27]=[C:26]([CH3:29])[CH:25]=5)[CH:22]=[CH:23][C:18]4=[N:17][N:16]=3)=[CH:8][CH:9]=[N:10]2)=[CH:5][CH:4]=1.[BrH:30].[OH-].[Na+]>>[BrH:30].[CH3:29][C:26]1[CH:25]=[C:24]([C:21]2[CH:22]=[CH:23][C:18]3[N:19]([C:15]([CH2:14][O:13][C:7]4[C:6]5[C:11](=[CH:12][C:3]([OH:2])=[CH:4][CH:5]=5)[N:10]=[CH:9][CH:8]=4)=[N:16][N:17]=3)[CH:20]=2)[O:28][N:27]=1

Participants

4

Reactant 3

HCID 260Hydrogen BromideHCID 14798Sodium HydroxideHCID 576910797-Methoxy-4-((6-(3-methylisoxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)quinoline

Product 1

HCID 1363872144-((6-(3-Methylisoxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)quinolin-7-ol hydrobromide

Procedure

A 150 mL tube was charged with 7-methoxy-4-((6-(3-methylisoxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)quinoline (1.44 g, 3.72 mmol) and HBr (30.3 ml, 558 mmol), sealed, then placed in a 120° C. for 5 hours. The reaction mixture was slowly neutralized with 6N NaOH until a precipitate crashed out of solution (pH ˜5)—the solid was collected to give 4-((6-(3-methylisoxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)quinolin-7-ol hydrobromide.

Workup

  1. customsealed
  2. customwas collected

Sources & evidence

ORD record
ord-28c3fde0a5cc4c9b926659dc07deeefc
Source dataset
uspto-grants-2012_06
Patent number
US08198448B2

Reaction notes

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