Sodium Carbonate → HCID 66717031, compound

HRID 2409588Notes

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.[C:11]([NH:14][C:15]1[CH:16]=[C:17](B(O)O)[CH:18]=[CH:19][CH:20]=1)(=[O:13])[CH3:12].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:20]=[C:15]([NH:14][C:11](=[O:13])[CH3:12])[CH:16]=[CH:17][CH:18]=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 (0.127 g, 0.4 mmol, 1 eq), 3-acetamidobenzeneboronic acid (0.091 g, 1.3 equiv, 1.3 eq), dichlorobis(triphenylphosphine)palladium(II) (0.055 g, 02 eq) and 2M aq Na2CO3 (1.1 ml) in dioxane (5 mL) was heated at 110° C. for 3 h. The solvent was removed under reduced pressure, redissolved in ethylacetate and washed with water. The organic layer was dried over Na2SO4, filtered and concentrated. The residue (0.167 g) was used in the next step of the synthesis without further purification. HPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.): tR=4.03 min, [M+H]+ m/z 385.1.

Workup

customThe solvent was removed under reduced pressure
dissolutionredissolved in ethylacetate
washwashed with water
dry with materialThe organic layer was dried over Na2SO4
filtrationfiltered
concentrationconcentrated
customThe residue (0.167 g) was used in the next step of the synthesis without further purification
customHPLC-MS (10-95% B in 4 min at 0.5 mL+2 min 100% B, flow 0.8 mL/min, 50° C.)

Sources & evidence

ORD record: ord-66cd389cd6c44d58b7b0169a6499c93f
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815918B2

Reaction notes

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