Hydrochloric Acid → HCID 66731691, compound

HRID 1963161Notes

Reaction equation

HRID 1963161 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[F:12][C:13]([F:24])([F:23])[C:14]1[N:19]=[CH:18][C:17](B(O)O)=[CH:16][CH:15]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CO.CC(OC)(C)C.Cl[Pd]Cl>[ClH:1].[F:12][C:13]([F:24])([F:23])[C:14]1[N:19]=[CH:18][C:17]([C:2]2[CH:3]=[C:4]([C:5]([O:7][CH3:8])=[O:6])[CH:9]=[CH:10][N:11]=2)=[CH:16][CH:15]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 2736842Methyl 2-chloropyridine-4-carboxylateHCID 251342782-(Trifluoromethyl)pyridine-5-boronic Acid

Product 1

HCID 66731691HCID 66731691, compoundYield 57.4%

Reagents, catalysts & solvents 3

HCID 24290Palladium ChlorideCatalystHCID 887MethanolSolventHCID 15413tert-Butyl methyl etherSolvent

Conditions

Temperature
100 °C

Procedure

Methyl 2-chloroisonicotinate (3 g, 17.48 mmol), 6-(trifluoromethyl)pyridin-3-yl boronic acid (5.01 g, 26.23 mmol), potassium carbonate (1.450 g, 10.49 mmol) and PdCl2 (dppf) (0.380 g, 0.52 mmol) were mixed in methanol (30 mL) in two separate 20 mL microwave vials. The vials were capped and heated at 100° C. for 10 min in a single node microwave reactor. Water and DCM were added and the phases were separated. The water phase (pH 9) was extracted with DCM and the combined organic phase washed with brine, passed through a phase separator and evaporated to yield an orange solid. The solid was diluted with MTBE, then HCl (4 M in dioxane) was added to give a suspension. The solids were collected by filtration to yield methyl 6′-(trifluoromethyl)-2,3′-bipyridine-4-carboxylate hydrochloride (3.2 g, 57%). MS m/z 283 (M+H)+

Workup

  1. customseparate 20 mL microwave vials
  2. customThe vials were capped
  3. additionWater and DCM were added
  4. customthe phases were separated
  5. extractionThe water phase (pH 9) was extracted with DCM
  6. washthe combined organic phase washed with brine
  7. customevaporated
  8. customto yield an orange solid
  9. customto give a suspension
  10. filtrationThe solids were collected by filtration

Sources & evidence

ORD record
ord-6f0eff80837246668986944c15f60cf0
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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