Sodium Carbonate → HCID 46941130, compound

HRID 2409584Notes

Reaction equation

I[C:2]1[N:9]2[C:5]([S:6][C:7]([C:10]3[CH:11]=[N:12][C:13]([CH3:16])=[CH:14][CH:15]=3)=[N:8]2)=[N:4][CH:3]=1.CC1(C)C(C)(C)OB([C:25]2[CH:26]=[C:27]([C:32]([F:35])([F:34])[F:33])[C:28]([NH2:31])=[N:29][CH:30]=2)O1.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>[CH3:16][C:13]1[N:12]=[CH:11][C:10]([C:7]2[S:6][C:5]3=[N:4][CH:3]=[C:2]([C:25]4[CH:26]=[C:27]([C:32]([F:35])([F:34])[F:33])[C:28]([NH2:31])=[N:29][CH:30]=4)[N:9]3[N:8]=2)=[CH:15][CH:14]=1

Participants

Conditions

Temperature: 110 °C

Procedure

A mixture of 5-Iodo-2-(6-methyl-pyridin-3-yl)-imidazo[2,1-b][1,3,4]thiadiazole (226 mg, 0.661 mmol, 1 eq), 5-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-3-trifluoromethyl-pyridin-2-ylamine (228 mg, 0.793 mmol, 1.2 eq), PdCl2(PPh3)2 (95 mg, 0.132 mmol, 0.2 eq) and 2M aq Na2CO3 (1.6 mL) in dioxane (7 mL) was heated at 110° C. for 90 min. The solvent was removed under reduced pressure and the residue was suspended in water and filtered. The solid was washed with diethylether, methanol and acetone. The residue was purified by HPLC to afford the desired product (4.7 mg, 2%). HPLC-MS (5-100% B in 8 min at 0.8 mL): tR=5.23 min, [M+H]+ m/z 377.0; 1H NMR (300 MHz, DMSO) δ 9.02 (s, 1H), 8.87 (s, 1H), 8.36 (s, 1H), 8.25 (dd, J=8.1, 2.2 Hz, 1H), 7.81 (s, 1H), 7.52 (d, J=8.2 Hz, 1H), 6.75 (s, 2H), 2.59 (s, 3H).

Workup

customThe solvent was removed under reduced pressure
filtrationfiltered
washThe solid was washed with diethylether, methanol and acetone
customThe residue was purified by HPLC

Sources & evidence

ORD record: ord-a9f76452079343bf8b9e5c2ac648789e
Source dataset: uspto-grants-2014_08
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08815918B2

Reaction notes

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