Triethylamine → HCID 86710135, compound

HRID 1468303Notes

Reaction equation

HRID 1468303 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([S:14](Cl)(=[O:16])=[O:15])=[C:9]([CH:11]([CH3:13])[CH3:12])[N:10]=[C:4]2[CH:3]=1.Cl.[F:19][C:20]1([F:24])[CH2:23][NH:22][CH2:21]1.C(N(CC)CC)C.C(=O)([O-])O.[Na+]>C(#N)C>[Br:1][C:2]1[CH:7]=[CH:6][N:5]2[C:8]([S:14]([N:22]3[CH2:23][C:20]([F:24])([F:19])[CH2:21]3)(=[O:16])=[O:15])=[C:9]([CH:11]([CH3:13])[CH3:12])[N:10]=[C:4]2[CH:3]=1

Participants

6

Reactant 4

HCID 8471TriethylamineHCID 516892Sodium BicarbonateHCID 27582473,3-Difluoroazetidine hydrochlorideHCID 86710134HCID 86710134, compound

Product 1

HCID 86710135HCID 86710135, compoundYield 94%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Conditions

Temperature
50 °C

Procedure

7-Bromo-2-isopropylimidazo[1,2-a]pyridine-3-sulfonylchloride (500 mg, 1.481 mmol) obtained in step 1 was dissolved in acetonitrile (5.0 mL), and the solution was stirred at 50° C. for 30 minutes after adding 3,3-difluoroazetidine hydrochloride (230 mg, 1.78 mmol) and triethylamine (0.413 ml, 2.96 mmol). The reaction mixture was allowed to cool to room temperature, and a sodium hydrogen carbonate aqueous solution was added. The precipitated solid was collected by filteration to give 7-bromo-3-(3,3-difluoroazetidin-1-ylsulfonyl)-2-isopropylimidazo[1,2-a]pyridine (546 mg, yield 94%).

Workup

  1. temperatureto cool to room temperature
  2. customThe precipitated solid was collected by filteration

Sources & evidence

ORD record
ord-f809d4ca10604c079b61ee048ebee3c2
Source dataset
uspto-grants-2015_04
Patent number
US09000186B2

Reaction notes

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