1,2-Dichloroethane → 5-(3-Chloro-4-isopropoxyphenyl)-3-(1H-indol-5-yl)-1,2,4-oxadiazole

HRID 710421Notes

Reaction equation

[Cl:1][C:2]1[CH:3]=[C:4]([CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13])[C:5]([OH:7])=O.O[NH:16][C:17](C1C2C=CNC=2C=CC=1)=[NH:18].C(Cl)CCl.C1C=CC2N(O)N=NC=2C=1.CCCC[N+:46]([CH2:55][CH2:56][CH2:57][CH3:58])([CH2:51][CH2:52][CH2:53][CH3:54])CCCC.[F-]>CN(C=O)C.C1COCC1.O>[Cl:1][C:2]1[CH:3]=[C:4]([C:5]2[O:7][N:18]=[C:17]([C:54]3[CH:58]=[C:57]4[C:51](=[CH:52][CH:53]=3)[NH:46][CH:55]=[CH:56]4)[N:16]=2)[CH:8]=[CH:9][C:10]=1[O:11][CH:12]([CH3:14])[CH3:13]

Participants

Conditions

Temperature: 120 °C

Procedure

A mixture of the product of Step A (0.31 g, 1.44 mmol), the product of Example 34, Step A (0.25 g, 1.44 mmol), EDC (0.36 g, 1.87 mmol) and HOBT (0.01 g) in anhydrous DMF (1 ml) was stirred overnight at 40° C. 1M solution of TBAF in THF (0.25 mL) was added to it and mixture was stirred for 3 h at 120° C. This was diluted to 20 ml with H2O and extracted with EtOAc (50 ml). The organic layer was separated, dried over MgSO4 and filtered. The filtrate was evaporated to dryness and the residue was purified by FCC (SiO2) and crystallized from MeOH to give the title compound (0.17 g; 33.3%) as creamy crystalline solid. 1H-NMR (CDCl3) 1.43 (d, 6H, J=6.06 Hz); 7.65-7.74 (m, 1H); 7.05 (d, 1H, J=8.76 Hz); 7.3-7.38 (m, 3H); 7.55 (d, 1H, J=8.14 Hz); 8.1-8.03 (m, 2H); 8.28 (d, 1H, J=2.13 Hz); 8.4 (broad s, 1H).

Workup

extractionextracted with EtOAc (50 ml)
customThe organic layer was separated
dry with materialdried over MgSO4
filtrationfiltered
customThe filtrate was evaporated to dryness
customthe residue was purified by FCC (SiO2)
customcrystallized from MeOH

Sources & evidence

ORD record: ord-0b80476d820544aab1efc5e7c280a995
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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