Water → 3-(3-iodo-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,2,4-oxadiazol-5-amine

HRID 634285Notes

Reaction equation

[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:15]=[C:14](C(Cl)(Cl)Cl)[O:13][N:12]=3)[CH:9]=2)[N:4]([S:20]([C:23]2[CH:29]=[CH:28][C:26]([CH3:27])=[CH:25][CH:24]=2)(=[O:22])=[O:21])[CH:3]=1.[CH:30]([NH2:33])([CH3:32])[CH3:31].O>CS(C)=O>[I:1][C:2]1[C:10]2[C:5](=[CH:6][CH:7]=[C:8]([C:11]3[N:15]=[C:14]([NH:33][CH:30]([CH3:32])[CH3:31])[O:13][N:12]=3)[CH:9]=2)[N:4]([S:20]([C:23]2[CH:24]=[CH:25][C:26]([CH3:27])=[CH:28][CH:29]=2)(=[O:22])=[O:21])[CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

To a solution of 3-(3-iodo-1-tosyl-1H-indol-5-yl)-5-(trichloromethyl)-1,2,4-oxadiazole (600 mg, 1.03 mmol) in DMSO (6 mL) was added isopropyl amine (1.2 mL). The reaction was heated to 90° C. in a sealed tube for 12 h then cooled to RT. The mixture was treated with water and extracted with EtOAc (2×20 mL). The organic layer was dried over anhydrous Na2SO4, and concentrated in vacuo. The residue was purified with basic alumina column chromatography (eluent: 35% EtOAc in petroleum ether) to give 3-(3-iodo-1-tosyl-1H-indol-5-yl)-N-isopropyl-1,2,4-oxadiazol-5-amine (450 mg, 83.3%) as an off brown solid. MS (ESI, pos. ion) m/z: 523.0 (M+1); 1H NMR (400 MHz, DMSO-d6): δ 9.44 (d, J=7.6 Hz, 1H), 8.18 (s, 1H), 8.09-8.07 (m, 1H), 7.96-7.93 (m, 3H), 7.83 (d, J=1.2 Hz, 1H), 7.42 (d, J=8.0 Hz, 1H), 3.88-3.83 (m, 1H), 2.32 (s, 3H), 1.22 (d, J=6.4 Hz, 6H).

Workup

temperaturethen cooled to RT
extractionextracted with EtOAc (2×20 mL)
dry with materialThe organic layer was dried over anhydrous Na2SO4
concentrationconcentrated in vacuo
customThe residue was purified with basic alumina column chromatography (eluent: 35% EtOAc in petroleum ether)

Sources & evidence

ORD record: ord-d0f7e070791f450cb7f951436c2b1d58
Source dataset: uspto-grants-2016_04
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09321756B2

Reaction notes

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