Hydrochloric Acid → HCID 66731716, compound

HRID 1963137Notes

Reaction equation

HRID 1963137 reaction equation
Br[C:2]1[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=1)[C:5]([O:7][CH3:8])=[O:6].[Cl:12][C:13]1[CH:18]=[CH:17][C:16](B(O)O)=[CH:15][CH:14]=1.C(=O)([O-])[O-].[K+].[K+].Cl>CO.CC(OC)(C)C.Cl[Pd]Cl>[ClH:12].[Cl:12][C:13]1[CH:18]=[CH:17][C:16]([C:2]2[CH:3]=[C:4]([CH:9]=[CH:10][N:11]=2)[C:5]([O:7][CH3:8])=[O:6])=[CH:15][CH:14]=1

Participants

8

Reactant 4

HCID 313Hydrochloric AcidHCID 11430Potassium CarbonateHCID 742994-Chlorophenylboronic acidHCID 38477682-Bromo-isonicotinic acid methyl ester

Product 1

HCID 66731716HCID 66731716, compoundYield 128.6%

Reagents, catalysts & solvents 3

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

Conditions

Temperature
100 °C

Procedure

Methyl 2-bromoisonicotinate (3.39 g, 15.69 mmol), 4-chlorophenylboronic acid (3.68 g, 23.54 mmol), potassium carbonate (3.25 g, 23.54 mmol) and PdCl2 (dppf) (0.341 g, 0.47 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 dissolved in MTBE, then HCl (4 M in dioxane) was added to give crude methyl 2-(4-chlorophenyl)isonicotinate hydrochloride (4.3 g). MS m/z 248 (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

Sources & evidence

ORD record
ord-d9d4d3b1fee840719d6dc24ba968faa9
Source dataset
uspto-grants-2013_04
Patent number
US08415378B2

Reaction notes

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