4-Methoxybenzenethiol → 4-[1-Ethyl-7-(4-methoxy-phenylsulfanyl)-1H-imidazo[4,5-c]pyridin-2-yl]-furazan-3-ylamine

HRID 1394194Notes

Reaction equation

Br[C:2]1[C:3]2[N:10]([CH2:11][CH3:12])[C:9]([C:13]3[C:14]([NH2:18])=[N:15][O:16][N:17]=3)=[N:8][C:4]=2[CH:5]=[N:6][CH:7]=1.C1(P(C2C=CC=CC=2)C2C=CC3C(=CC=CC=3)C=2C2C3C(=CC=CC=3)C=CC=2P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:65][O:66][C:67]1[CH:72]=[CH:71][C:70]([SH:73])=[CH:69][CH:68]=1.CC(C)([O-])C.[Na+]>O1CCOCC1.C1(C)C=CC=CC=1.C(OCC)(=O)C.CO>[CH2:11]([N:10]1[C:3]2[C:2]([S:73][C:70]3[CH:71]=[CH:72][C:67]([O:66][CH3:65])=[CH:68][CH:69]=3)=[CH:7][N:6]=[CH:5][C:4]=2[N:8]=[C:9]1[C:13]1[C:14]([NH2:18])=[N:15][O:16][N:17]=1)[CH3:12]

Participants

Conditions

Temperature: 175 °C

Procedure

Under Ar, a solution of the product from Example 100 (53.2 mg, 172 mol) in 1,4-dioxane (1 ml) and toluene (1.5 ml) was treated with Tris(dibenzylidene-acetone)dipalladium (15 mg, 17 mol), racemic-2,2′-Bis(diphenylphosphino)-1,1′-binaphthyl (20 mg, 34 mol), 4-methoxybenzenethiol (26 l, 206 mol), and sodium tert-butoxide (23.5 mg, 241 mol). This mixture was then heated to 175° C. by microwave for 1 h. After cooled to ambient temperture, the reaction mixture was diluted with ethyl acetate (30 ml) and methanol (30 ml), filtered though a celite pad and then the filtrate was concentrated in vacuo. The residue was purified with flash chromatography (hexanes/ethyl acetate 2:1), to afford the title compound, (35.6 mg, 56%); MS (ES+) m/e 369 [M+H]+.

Workup

temperatureAfter cooled to ambient temperture
filtrationfiltered though a celite pad
concentrationthe filtrate was concentrated in vacuo
customThe residue was purified with flash chromatography (hexanes/ethyl acetate 2:1)

Sources & evidence

ORD record: ord-41150ff1e811499f96801fdfda4141e6
Source dataset: uspto-grants-2008_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07348339B2

Reaction notes

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