Cesium carbonate → HCID 67232888, compound

HRID 876479Notes

Reaction equation

HRID 876479 reaction equation
Cl[C:2]1[CH:11]=[CH:10][C:9]2[C:4](=[C:5]([F:12])[CH:6]=[CH:7][CH:8]=2)[N:3]=1.[N:13]1[N:14]=[CH:15][N:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=12.C([O-])([O-])=O.[Cs+].[Cs+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[N:13]1[N:14]=[C:15]([C:2]2[CH:11]=[CH:10][C:9]3[C:4](=[C:5]([F:12])[CH:6]=[CH:7][CH:8]=3)[N:3]=2)[N:16]2[CH:21]=[CH:20][CH:19]=[CH:18][C:17]=12

Participants

6

Reactant 3

HCID 10796Cesium carbonateHCID 249770[1,2,4]Triazolo[4,3-a]pyridineHCID 221251942-Chloro-8-fluoroquinoline

Product 1

HCID 67232888HCID 67232888, compound

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Procedure

2-Chloro-8-fluoroquinoline (0.75 g, 4.13 mmol) was combined with [1,2,4]triazolo[4,3-a]pyridine (0.541 g, 4.54 mmol), micronized Cs2CO3 (2.69 g, 8.26 mmol), and PdCl2(PPh3)2 (0.290 g, 0.413 mmol) then the mixture was slurried in dioxane (20 mL). The reaction was deoxygenated with argon and heated to reflux for 20 hours, then cooled, diluted with CHCl3 and filtered through a pad of Celite®. The filtrate was concentrated onto Na2SO4 powder (15 g) and the mixture was chromatographed on SiO2 eluting with a stepped gradient of 0-2% MeOH/ethyl acetate. The desired product was isolated as a cream-colored solid (1.12 g). MS APCI (+) m/z 265.3 (M+1) detected.

Workup

  1. customThe reaction was deoxygenated with argon
  2. temperatureheated
  3. temperatureto reflux for 20 hours
  4. temperaturecooled
  5. additiondiluted with CHCl3
  6. filtrationfiltered through a pad of Celite®
  7. concentrationThe filtrate was concentrated onto Na2SO4 powder (15 g)
  8. customthe mixture was chromatographed on SiO2 eluting with a stepped gradient of 0-2% MeOH/ethyl acetate

Sources & evidence

ORD record
ord-e7c9d7c2d836414786981012c3b185af
Source dataset
uspto-grants-2015_03
Patent number
US08987251B2

Reaction notes

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