Potassium Carbonate → HCID 66717033, compound

HRID 2409573Notes

Reaction equation

HRID 2409573 reaction equation
Br[C:2]1[S:6][C:5]2=[N:7][CH:8]=[C:9]([I:10])[N:4]2[N:3]=1.[CH3:11][C:12]1[CH:17]=[CH:16][N:15]=[CH:14][C:13]=1B(O)O.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.C(Cl)Cl.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2]>[I:10][C:9]1[N:4]2[C:5]([S:6][C:2]([C:13]3[CH:14]=[N:15][CH:16]=[CH:17][C:12]=3[CH3:11])=[N:3]2)=[N:7][CH:8]=1

Participants

7

Reactant 3

HCID 11430Potassium CarbonateHCID 27627114-Methylpyridine-3-Boronic AcidHCID 662215402-Bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole

Product 1

HCID 66717033HCID 66717033, compoundYield 96.1%

Reagents, catalysts & solvents 3

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6344DichloromethaneSolventHCID 312751,4-DioxaneSolvent

Conditions

Temperature
110 °C

Procedure

A mixture of 2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole (50 mg, 0.152 mmol), 4-methylpyridine-3-boronic acid (23 mg, 0.167 mmol), PdCl2(dppf) (25 mg, 0.03 mmol) and sat. aq. K2CO3 (0.25 ml) in dioxane (0.5 mL) was heated at 110° C. overnight. The reaction mixture was cooled, diluted with DCM and washed with water. The organic layer was dried (Na2SO4), filtered and evaporated. The residue was purified by column chromatography (MeOH/DCM, 0% to 40%) to give the desired product (50 mg, 96%). HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=3.75 min, [M+H]+ m/z 343.1.

Workup

  1. temperatureThe reaction mixture was cooled
  2. washwashed with water
  3. dry with materialThe organic layer was dried (Na2SO4)
  4. filtrationfiltered
  5. customevaporated
  6. customThe residue was purified by column chromatography (MeOH/DCM, 0% to 40%)

Sources & evidence

ORD record
ord-6a07928c026648449ea7630128b05fcd
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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