Sodium Carbonate → HCID 86644345, compound

HRID 383314Notes

Reaction equation

HRID 383314 reaction equation
Br[C:2]1[N:6]2[CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=[CH:10][C:5]2=[N:4][CH:3]=1.[Cl:15][C:16]1[CH:21]=[C:20](B(O)O)[CH:19]=[CH:18][N:17]=1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.O.C1(C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)[Pd][P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[Cl:15][C:16]1[C:21]([C:2]2[N:6]3[CH:7]=[C:8]([C:11]([F:14])([F:13])[F:12])[CH:9]=[CH:10][C:5]3=[N:4][CH:3]=2)=[CH:20][CH:19]=[CH:18][N:17]=1

Participants

7

Reactant 3

HCID 10340Sodium CarbonateHCID 51515952-Chloropyridine-4-boronic acidHCID 455882283-Bromo-6-(trifluoromethyl)imidazo[1,2-a]pyridine

Product 1

HCID 86644345HCID 86644345, compound

Reagents, catalysts & solvents 3

HCID 178419050HCID 178419050, compoundCatalystHCID 962WaterSolvent2×HCID 312751,4-DioxaneSolvent

Conditions

Temperature
95 °C

Procedure

To a solution of 3-Bromo-6-trifluoromethyl-imidazo[1,2-a]pyridine (1 eq, 2.9 mmol, 0.77 g), 2-chloropyrid-4-yl boronic acid (1.05 eq, 3.05 mmol, 0.478 g), Na2CO3 (2 eq, 5.81 mmol, 0.616 g) in dioxane (45 ml) and water (13.5 ml), under an inert atmosphere of argon is added bis(triphenylphosphine)palladium II chloride (0.1 eq, 0.03 mmol, 200 mg). The reaction mixture is heated at 95° C. for 16 hours. The mixture is diluted with H2O (50 ml) and extracted with EtOAc. The combined organic portions are washed with brine, dried (MgSO4) and concentrated in vacuo. The residue is purified by chromatography on silica eluting with 0-10% MeOH in EtOAc to afford the title compound; [M+H]+=297/299.

Workup

  1. extractionextracted with EtOAc
  2. washThe combined organic portions are washed with brine
  3. dry with materialdried (MgSO4)
  4. concentrationconcentrated in vacuo
  5. customThe residue is purified by chromatography on silica eluting with 0-10% MeOH in EtOAc

Sources & evidence

ORD record
ord-4718c484ac6740b09a5e8cca5e1356b0
Source dataset
uspto-grants-2013_02
Patent number
US08367662B2

Reaction notes

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