Pyridine → 6-Bromo-2-(4-methanesulfonyl-benzyl)-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridine

HRID 1497763Notes

Reaction equation

HRID 1497763 reaction equation
[Br:1][C:2]1[C:3]([CH3:33])=[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)[C:5]([NH:8][C:9](=[N:21]O)[CH2:10][C:11]2[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=2)=[N:6][CH:7]=1.N1C=CC=CC=1.C1(C)C=CC(S(Cl)(=O)=O)=CC=1.C(=O)([O-])O.[Na+]>C1(C)C=CC=CC=1>[Br:1][C:2]1[C:3]([CH3:33])=[C:4]([C:23]2[CH:28]=[CH:27][CH:26]=[C:25]([C:29]([F:32])([F:31])[F:30])[CH:24]=2)[C:5]2[N:6]([N:21]=[C:9]([CH2:10][C:11]3[CH:16]=[CH:15][C:14]([S:17]([CH3:20])(=[O:19])=[O:18])=[CH:13][CH:12]=3)[N:8]=2)[CH:7]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 73974-Toluenesulfonyl chlorideHCID 516892Sodium BicarbonateHCID 178421702HCID 178421702, compound

Product 1

HCID 867080996-Bromo-2-(4-methanesulfonyl-benzyl)-7-methyl-8-(3-trifluoromethyl-phenyl)-[1,2,4]triazolo[1,5-a]pyridineYield 102.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
0 °C

Procedure

A suspension of N-[5-bromo-4-methyl-3-(3-trifluoromethyl-phenyl)-pyridin-2-yl]-N′-hydroxy-2-(4-methanesulfonyl-phenyl)-acetamidine (Int. 12, 165 mg, 0.304 mmol) in toluene (6 mL) and pyridine (98 μL, 1.218 mmol) was cooled to 0° C. and p-toluenesulfonyl chloride (232 mg, 1.218 mmol) was added. The reaction mixture was stirred at 0° C. for 25 mins then at RT for 6 days. Sodium hydrogen carbonate (saturated solution, 30 mL) was added and the mixture was extracted with DCM (2×30 mL). The organic phase was concentrated and the resultant residue purified by flash chromatography eluting with a gradient of 0-100% EtOAc in cyclohexane to give the title compound as a yellow solid (164 mg).

Workup

  1. waitat RT for 6 days
  2. extractionthe mixture was extracted with DCM (2×30 mL)
  3. concentrationThe organic phase was concentrated
  4. customthe resultant residue purified by flash chromatography
  5. washeluting with a gradient of 0-100% EtOAc in cyclohexane

Sources & evidence

ORD record
ord-5922bfe049d04642b5809b773795ebf3
Source dataset
uspto-grants-2015_12
Patent number
US09199984B2

Reaction notes

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