Hydrogen Bromide → HCID 178524400, compound

HRID 2262813Notes

Reaction equation

HRID 2262813 reaction equation
[NH2:1][C:2]1[CH:6]=[C:5]([S:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[C:11]([O:13]CC)=[O:12])[NH:4][N:3]=1.Cl[C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][N:21]=1.Br.[OH-].[Na+]>C(O)(C)C.O>[N:21]1[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=1[NH:1][C:2]1[CH:6]=[C:5]([S:7][C:8]2[CH:9]=[C:10]([CH:16]=[CH:17][CH:18]=2)[C:11]([OH:13])=[O:12])[NH:4][N:3]=1

Participants

7

Reactant 4

HCID 260Hydrogen BromideHCID 79772-ChloropyridineHCID 14798Sodium HydroxideHCID 178468953HCID 178468953, compound

Product 1

HCID 178524400HCID 178524400, compoundYield 63.5%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 3776IsopropanolSolvent

Conditions

Temperature
175 °C

Procedure

A stirred solution of ethyl 3-(3-amino-1H-pyrazol-5-ylthio)benzoate (0.150 g, 0.57 mmol), 2-chloropyridine (0.130 g, 1.14 mmol) in isopropanol (2 mL) was treated with hydrobromic acid (0.150 mL) and heated at 175° C. in a microwave oven for 30 minutes. The mixture was then diluted with water (1.5 mL) and treated with sodium hydroxide (1 pellet). The reaction was stirred at room temperature overnight, then concentrated to dryness. The residue was dissolved in methanol, acidified with conc. hydrochloric acid and purified on Prep HPLC (MeCN/H2O/5 mM NH4OAc) to give the title material (0.113 g, 62%) as a solid. The compound was used as such in the next reaction.

Workup

  1. concentrationconcentrated to dryness
  2. dissolutionThe residue was dissolved in methanol
  3. custompurified on Prep HPLC (MeCN/H2O/5 mM NH4OAc)

Sources & evidence

ORD record
ord-5ee498aabe3548fd857fa7c5dd38c888
Source dataset
uspto-grants-2010_12
Patent number
US07851500B2

Reaction notes

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