Sodium Carbonate → 5-Iodo-2-[4-(morpholine-4-sulfonyl)-phenyl]-imidazo[2,1-b][1,3,4]thiadiazole

HRID 2409585Notes

Reaction equation

HRID 2409585 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.[N:11]1([S:17]([C:20]2[CH:25]=[CH:24][C:23](B(O)O)=[CH:22][CH:21]=2)(=[O:19])=[O:18])[CH2:16][CH2:15][O:14][CH2:13][CH2:12]1.C([O-])([O-])=O.[Na+].[Na+]>O1CCOCC1.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1>[I:10][C:9]1[N:4]2[C:5]([S:6][C:2]([C:23]3[CH:24]=[CH:25][C:20]([S:17]([N:11]4[CH2:12][CH2:13][O:14][CH2:15][CH2:16]4)(=[O:18])=[O:19])=[CH:21][CH:22]=3)=[N:3]2)=[N:7][CH:8]=1

Participants

6

Reactant 3

HCID 10340Sodium CarbonateHCID 441195464-(Morpholin-4-ylsulphonyl)benzeneboronic acidHCID 662215402-Bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole

Product 1

HCID 667171205-Iodo-2-[4-(morpholine-4-sulfonyl)-phenyl]-imidazo[2,1-b][1,3,4]thiadiazoleYield 42.5%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 312751,4-DioxaneSolvent

Conditions

Temperature
90 °C

Procedure

A mixture of 2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole (200 mg, 0.44 mmol), 4-(4-morpholinylsulfonyl)phenylboronic acid (144 mg, 0.52 mmol), PdCl2(PPh3)2 (60 mg, 0.088 mmol) and 2M aq Na2CO3 (1.2 mL) in dioxane (8 mL) was heated at 90° C. for 18 h. The solvent was removed in vacuo and the residue was triturated from EtOAc and filtered. The filtrate was evaporated and the residue was recrystallyzed from MeOH to give the desired product (89 mg, 31%) as a brown solid.

Workup

  1. customThe solvent was removed in vacuo
  2. customthe residue was triturated from EtOAc
  3. filtrationfiltered
  4. customThe filtrate was evaporated

Sources & evidence

ORD record
ord-7540ac21b2904eb4ba1f199a14999810
Source dataset
uspto-grants-2014_08
Patent number
US08815918B2

Reaction notes

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