Sodium Carbonate → 3-(5-Iodo-imidazo[2,1-b][1,3,4]thiadiazol-2-yl)-benzamide

HRID 2409569Notes

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.[NH2:11][C:12]([C:14]1[CH:15]=[C:16](B(O)O)[CH:17]=[CH:18][CH:19]=1)=[O:13].C([O-])([O-])=O.[Na+].[Na+].C([O-])(O)=O.[Na+]>O1CCOCC1.O.C(Cl)Cl.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:18]3[CH:19]=[C:14]([CH:15]=[CH:16][CH:17]=3)[C:12]([NH2:11])=[O:13])=[N:3]2)=[N:7][CH:8]=1

Participants

Conditions

Temperature: 90 °C

Procedure

A mixture of 2-bromo-5-iodoimidazo[2,1-b][1,3,4]thiadiazole (150 mg, 0.45 mmol), 3-aminocarbonylphenylboronic acid (85 mg, 0.50 mmol), PdCl2(PPh3)2 (32 mg, 0.045 mmol) and Na2CO3 (145 mg, 1.4 mmol) in dioxane (1.5 mL) and water (0.3 mL) was heated at 90° C. for 2 h. The reaction mixture was cooled and diluted with DCM (35 mL) and sat NaHCO3 (20 mL). The organic layer was washed with sat. NaHCO3 (3×20 mL) and brine (30 mL), dried over Na2SO4, filtered and concentrated in vacuo. The residue was triturated with diethylether and filtered to give the desired product (73 mg, 42%). HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=3.59 min, [M+H]+ m/z 371.1.

Workup

temperatureThe reaction mixture was cooled
washThe organic layer was washed with sat. NaHCO3 (3×20 mL) and brine (30 mL)
dry with materialdried over Na2SO4
filtrationfiltered
concentrationconcentrated in vacuo
customThe residue was triturated with diethylether
filtrationfiltered

Sources & evidence

ORD record: ord-0cca33da523540358101218538288a45
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815918B2

Reaction notes

Loading…