Sodium Carbonate → HCID 67283603, compound

HRID 2409577Notes

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.[NH:11]1[C:19]2[C:14](=[CH:15][C:16](B(O)O)=[CH:17][CH:18]=2)[CH:13]=[CH: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:16]3[CH:15]=[C:14]4[C:19](=[CH:18][CH:17]=3)[NH:11][CH:12]=[CH:13]4)=[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 (0.150 g, 0.455 mmol, 1 eq) and 5-indolylboronic acid (0.088 g, 0.546 mmol, 1.2 eq), 2M aq Na2CO3 (1 mL) and PdCl2(PPh3)2 (0.064 g, 0.091 mmol, 0.2 eq) in dioxane (5 mL) was heated at 110° C. for 2 h. The solvent was removed in vacuo, redissolved in DCM/water (150 mL) and extracted with DCM (2×80 mL). The combined organic layers were dried (MgSO4), filtered and evaporated. The residue was purified by column chromatography (20-70% EtOAc in cyclohexane) to afford the desired product (91 mg, 54%) as a yellow solid. HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=4.53 min, [M+H]+ m/z 367.0.

Workup

customThe solvent was removed in vacuo
dissolutionredissolved in DCM/water (150 mL)
extractionextracted with DCM (2×80 mL)
dry with materialThe combined organic layers were dried (MgSO4)
filtrationfiltered
customevaporated
customThe residue was purified by column chromatography (20-70% EtOAc in cyclohexane)

Sources & evidence

ORD record: ord-9370cbaf28f94281847f3946c8b269fb
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815918B2

Reaction notes

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