Potassium Carbonate → 5-[2-(3,4-Dimethoxy-phenyl)-imidazo[2,1-b][1,3,4]thiadiazol-5-yl]-pyridine-2-carbonitrile

HRID 2409553Notes

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.[C:26]([C:28]1[CH:33]=[CH:32][C:31](B2OC(C)(C)C(C)(C)O2)=[CH:30][N:29]=1)#[N:27].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:32]=[CH:33][C:28]([C:26]#[N:27])=[N:29][CH:30]=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), 2-cyanopyridine-5-boronic acid pinacol ester (0.155 g, 0.64 mmol, 2.5 eq), Pd(Ph3P)2Cl2 (0.018 g, 0.1 eq), potassium carbonate (0.178 g, 1.3 mmol, 5 eq), and water (2 mL) was heated in the microwave oven (120° C., 30 min) and was left to cool to RT. A precipitate formed that was filtered off (0.048 g) and washed with a mixture of Et2O and little MeOH to afford the desired product (white solid, 0.029 g, 31%). HPLC-MS: (5-100% B in 8 min, 0.8 mL/min, 50° C.): tR=5.37 min, [M+H]+ m/z 364.1; 1H NMR (300 MHz, DMSO) d 9.47-9.39 (m, 1H), 8.68 (dd, J=8.3, 2.3, 1H), 8.23-8.10 (m, 2H), 7.60 (dd, J=8.3, 2.3, 1H), 7.51 (d, J=2.1, 1H), 7.17 (d, J=8.5, 1H), 3.91 (s, 3H), 3.87 (s, 3H);

Workup

waitwas left
temperatureto cool to RT
customA precipitate formed
filtrationthat was filtered off (0.048 g)
washwashed with a mixture of Et2O and little MeOH

Sources & evidence

ORD record: ord-5a5724bcc18c4a488010363c8108d73c
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815918B2

Reaction notes

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