Water → 2-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-8-(neopentyloxy)quinoline

HRID 876395Notes

Reaction equation

HRID 876395 reaction equation
[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([OH:20])[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12.C(=O)([O-])[O-].[Cs+].[Cs+].[CH2:27](I)[C:28]([CH3:31])([CH3:30])[CH3:29].O>CC(N(C)C)=O>[N:1]1[N:2]=[C:3]([C:10]2[CH:19]=[CH:18][C:17]3[C:12](=[C:13]([O:20][CH2:27][C:28]([CH3:31])([CH3:30])[CH3:29])[CH:14]=[CH:15][CH:16]=3)[N:11]=2)[N:4]2[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=12

Participants

6

Reactant 4

HCID 962WaterHCID 10796Cesium carbonateHCID 84953Propane, 1-iodo-2,2-dimethyl-HCID 136337804HCID 136337804, compound

Product 1

HCID 583036472-([1,2,4]Triazolo[4,3-a]pyridin-3-yl)-8-(neopentyloxy)quinolineYield 49.1%

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 2-([1,2,4]triazolo[4,3-a]pyridin-3-yl)quinolin-8-ol (100 mg, 0.38 mmol), Example 1, Step D, in anhydrous DMA (2 mL) was added cesium carbonate (373 mg, 1.14 mmol) followed by neopentyl iodide (101 μL, 0.76 mmol). The heterogeneous mixture was stirred at ambient temperature for 2 hours then at 100° C. for 16 hours. The cooled mixture was treated with water (30 mL) and extracted with EtOAc (3×20 mL). The combined organic phases were washed with water and brine, dried over Na2SO4 and concentrated to afford a cream-colored solid. This was triturated with ether and the resulting solid collected by filtration and dried in vacuo to provide desired product (62 mg, 49%) as a white powder. MS ESI (+) m/z 333.3 (M+1) detected.

Workup

  1. waitat 100° C. for 16 hours
  2. extractionextracted with EtOAc (3×20 mL)
  3. washThe combined organic phases were washed with water and brine
  4. dry with materialdried over Na2SO4
  5. concentrationconcentrated
  6. customto afford a cream-colored solid
  7. customThis was triturated with ether
  8. filtrationthe resulting solid collected by filtration
  9. customdried in vacuo

Sources & evidence

ORD record
ord-b39de86bb09d41d2989df7916b5c7cb2
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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