Potassium Carbonate → HCID 66717025, compound

HRID 2409590Notes

Reaction equation

HRID 2409590 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][O:12][C:13]1[CH:14]=[N:15][CH:16]=[C:17](B2OC(C)(C)C(C)(C)O2)[CH:18]=1.C([O-])([O-])=O.[K+].[K+]>O1CCOCC1.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:17]3[CH:16]=[N:15][CH:14]=[C:13]([O:12][CH3:11])[CH:18]=3)=[N:3]2)=[N:7][CH:8]=1

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 38661613-Methoxy-5-(4,4,5,5-tetramethyl-1,3,2-dioxaborolan-2-yl)pyridineHCID 662215402-Bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole

Product 1

HCID 66717025HCID 66717025, compoundYield 24%

Reagents, catalysts & solvents 2

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

Conditions

Temperature
110 °C

Procedure

A mixture of 2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole (100 mg, 0.303 mmol, 1 eq), 3-methoxypyridine-5-boronic acid pinacol ester (78 mg, 0.333 mmol, 1 eq), PdCl2(dppf) (25 mg, 0.030 mmol, 0.1) and sat K2CO3 (0.6 mL) in dioxane (4 mL) was heated at 110° C. for 2 days. Additional amount of catalyst (0.05 eq) was added and the reaction mixture was heated under microwave irradiation at 130° C. for 2 h. The solvent was removed, the residue was diluted with EtOAc, sonicated and flushed through a plug of Celite. The filtrate was concentrated and the residue was purified by column chromatography (MeOH in DCM, 0 to 10%) to give the desired product (26 mg, 24%). HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=3.97 min, [M+H]+ m/z 359.0.

Workup

  1. temperaturethe reaction mixture was heated under microwave irradiation at 130° C. for 2 h
  2. customThe solvent was removed
  3. additionthe residue was diluted with EtOAc
  4. customsonicated
  5. customflushed through a plug of Celite
  6. concentrationThe filtrate was concentrated
  7. customthe residue was purified by column chromatography (MeOH in DCM, 0 to 10%)

Sources & evidence

ORD record
ord-88190d5c0aa3481bb36376e2826bcbb0
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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