Sodium Carbonate → HCID 66717014, compound

HRID 2409583Notes

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[CH:16]=[C:15](B2OC(C)(C)C(C)(C)O2)[CH:14]=[CH:13][C:12]=1[CH3:26].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:15]3[CH:16]=[N:11][C:12]([CH3:26])=[CH:13][CH:14]=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 (169 mg, 0.512 mmol, 1 eq), 2-picoline-5-boronic acid pinacol ester (137 mg, 0.614 mmol, 1.2 eq), PdCl2(PPh3)2 (73 mg, 0.102 mmol, 0.2 eq) and 2M aq Na2CO3 (1.5 mL) in dioxane (7 mL) was heated at 110° C. for 2 h. The solvent was removed under reduced pressure, redissolved in dichloromethane and washed with water. The organic layer was dried over Na2SO4 and concentrated. The residue (226. mg) 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 mUrnin, 50° C.): tR=3.79 min, [M+H]+ m/z 342.9.

Workup

customThe solvent was removed under reduced pressure
dissolutionredissolved in dichloromethane
washwashed with water
dry with materialThe organic layer was dried over Na2SO4
concentrationconcentrated
customThe residue (226. mg) 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 mUrnin, 50° C.)

Sources & evidence

ORD record: ord-9aca8dac3b5c46e499edac28c0054835
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815918B2

Reaction notes

Loading…