Potassium Carbonate → 2,5-Bis-(3,4-dimethoxy-phenyl)-imidazo[2,1-b][1,3,4]thiadiazole

HRID 2409552Notes

Reaction equation

[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:15][C:14]3=[N:16][CH:17]=[C:18](I)[N:13]3[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10].O1CCOCC1.[CH3:26][O:27][C:28]1[CH:29]=[C:30](B(O)O)[CH:31]=[CH:32][C:33]=1[O:34][CH3:35].C([O-])([O-])=O.[K+].[K+]>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.O>[CH3:1][O:2][C:3]1[CH:4]=[C:5]([C:11]2[S:15][C:14]3=[N:16][CH:17]=[C:18]([C:31]4[CH:30]=[CH:29][C:28]([O:27][CH3:26])=[C:33]([O:34][CH3:35])[CH:32]=4)[N:13]3[N:12]=2)[CH:6]=[CH:7][C:8]=1[O:9][CH3:10]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of 2-(3,4-dimethoxy-phenyl)-5-iodo-imidazo[2,1-b][1,3,4]thiadiazole (0.10 g, 0.3 mmol, 1 eq), dioxane (5 mL), 3,4-dimethoxyphenylboronic acid (0.12 g, 0.6 mmol, 2.5 eq), Pd(Ph3P)2Cl2 (0.018 g, 0.1 eq), K2CO3 (0.178 g, 1.3 mmol, 5 eq) and water (2 mL) was heated in the microwave oven (120° C., 30 min). The reaction mixture was concentrated, and the residue was purified by column chromatography (SiO2, cyclohexane/5-100% EtOAc). The obtained product was triturated with MeOH/Et2O to give the desired product (yellow solid, 0.026 g, 26%). HPLC-MS: (5-100% B in 10 min, 0.6 mL/min, 50° C.): tR=7.24 min, [M+H]+ m/z 398.1; 1H NMR (300 MHz, DMSO) δ/ppm 7.74 (s, 1H), 7.70 (d, J=2.0, 1H), 7.61 (dd, J=2.0, 8.4, 1H), 7.57-7.50 (m, 2H), 7.17 (d, J=8.2, 1H), 7.09 (d, J=8.5, 1H), 3.88 (s, 6H), 3.86 (s, 3H), 3.81 (s, 3H).

Workup

concentrationThe reaction mixture was concentrated
customthe residue was purified by column chromatography (SiO2, cyclohexane/5-100% EtOAc)
customThe obtained product was triturated with MeOH/Et2O

Sources & evidence

ORD record: ord-1a1a0751d550400ab867f2fa39c12fb4
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815918B2

Reaction notes

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