Sodium Carbonate → HCID 66717127, compound

HRID 2409579Notes

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][S:12]([C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)(=[O:14])=[O:13].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:19]3[CH:18]=[CH:17][CH:16]=[C:15]([S:12]([CH3:11])(=[O:14])=[O:13])[CH:20]=3)=[N:3]2)=[N:7][CH:8]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole (0.20 g, 0.606 mmol, 1 eq), 3-(methylsulfonyl)phenylboronic acid (0.182 g, 0.909 mmol, 1.5 eq), PdCl2(PPh3)2 (0.085 g, 0.121 mmol, 0.2 eq) and 2M Na2CO3 (1.0 mL) in dioxane (5 mL) was heated at 110° C. for 24 h. More PdCl2(PPh3)2 (0.1 eq) was added and the reaction mixture was heated at 110° C. for 4 h. The solvent was removed, water was added and the mixture was extracted with DCM. The organic layer was dried (MgSO4), filtered and evaporated. The residue was triturated from MeOH and filtered to give the desired product (91 mg, 37%) as an orange solid. It was used in the next step of the synthesis with no further treatment. HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=3.98 min, [M+H]+ m/z 405.9.

Workup

temperaturethe reaction mixture was heated at 110° C. for 4 h
customThe solvent was removed
additionwater was added
extractionthe mixture was extracted with DCM
dry with materialThe organic layer was dried (MgSO4)
filtrationfiltered
customevaporated
customThe residue was triturated from MeOH
filtrationfiltered

Sources & evidence

ORD record: ord-1026b944a02042988125f9a539338776
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815918B2

Reaction notes

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