1,2-Dichloroethane → 3-(1H-indol-4-yl)-5-(6-propylpyridin-3-yl)-1,2,4-oxadiazole

HRID 710474Notes

Reaction equation

[OH:1][NH:2][C:3]([C:5]1[C:6]2[CH:7]=[CH:8][NH:9][C:10]=2[CH:11]=[CH:12][CH:13]=1)=[NH:4].[CH2:14]([C:17]1[CH:25]=[CH:24][C:20]([C:21](O)=O)=[CH:19][N:18]=1)[CH2:15][CH3:16].C(Cl)CCl.CCCC[N+](CCCC)(CCCC)CCCC.[F-]>CS(C)=O.C1COCC1.CCOC(C)=O>[NH:9]1[C:10]2[C:6](=[C:5]([C:3]3[N:4]=[C:21]([C:20]4[CH:19]=[N:18][C:17]([CH2:14][CH2:15][CH3:16])=[CH:25][CH:24]=4)[O:1][N:2]=3)[CH:13]=[CH:12][CH:11]=2)[CH:7]=[CH:8]1

Participants

Conditions

Temperature: 40 °C

Procedure

A mixture of the product of Example 34, Step A (0.087 g; 0.5 mmol), 6-propylnicotinic acid (0.082 g; 0.5 mmol) and EDC (0.11 g; 0.57 mmol) in anhydrous DMSO (2 ml) was stirred for 1 h at ˜40° C. under N2. To this 1M TBAF in THF (0.5 ml) was added and the resulting mixture was stirred for 1 h at ˜110° C. After cooling to room temperature the mixture was diluted to 15 ml with EtOAc, washed with H2O, brine, dried over anhydrous MgSO4, filtered and filtrate evaporated to dryness. The residue was purified by FCC (SiO2, CH2Cl2:EtOAc 9:1) to give the title compound (0.05 g; 33%), as colorless solid. 1H-NMR (CDCl3) 1.0 (m, 3H); 1.8 (m, 2H); 2.88 (tr, 2H, J=9 Hz); 7.3-7.4 (m, 4H); 7.57 (d, 1H, J=9 Hz); 8.08 (dd, 1H, J=2, 9 Hz); 8.38-8.43 (m, 2H); 9.39 (d, 1H, J=2 Hz).

Workup

stirringthe resulting mixture was stirred for 1 h at ˜110° C
temperatureAfter cooling to room temperature the mixture
washwashed with H2O, brine
dry with materialdried over anhydrous MgSO4
filtrationfiltered
customfiltrate evaporated to dryness
customThe residue was purified by FCC (SiO2, CH2Cl2:EtOAc 9:1)

Sources & evidence

ORD record: ord-b97a3aea02574e62a440f405d62f0e19
Source dataset: uspto-grants-2015_11
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09181182B2

Reaction notes

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