Acetonitrile → HCID 86620685, compound

HRID 913562Notes

Reaction equation

[F:1][C:2]([F:19])([F:18])[C:3]1[NH:4][C:5]2[C:10]([CH:11]=1)=[C:9]([C:12]([F:15])([F:14])[F:13])[C:8]([C:16]#[N:17])=[CH:7][CH:6]=2.C([O-])([O-])=O.[Cs+].[Cs+].Cl[CH2:27][C:28]1[N:32]=[C:31]([C:33]2[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:41])[F:40])[CH:34]=2)[O:30][N:29]=1.CC#N>CCOC(C)=O>[F:19][C:2]([F:1])([F:18])[C:3]1[N:4]([CH2:27][C:28]2[N:32]=[C:31]([C:33]3[CH:38]=[CH:37][CH:36]=[C:35]([C:39]([F:42])([F:40])[F:41])[CH:34]=3)[O:30][N:29]=2)[C:5]2[C:10]([CH:11]=1)=[C:9]([C:12]([F:14])([F:15])[F:13])[C:8]([C:16]#[N:17])=[CH:7][CH:6]=2

Participants

Conditions

Temperature: 75 °C

Procedure

A mixture of 2,4-bis(trifluoromethyl)-1H-indole-5-carbonitrile (0.050 g, 0.18 mmol), Cs2CO3 (0.064 g, 0.20 mmol.), 3-(chloromethyl)-5-[3-(trifluoromethyl)phenyl]-1,2,4-oxadiazole (0.052 g, 0.20 mmol.) and CH3CN (4 mL) was stirred at 75° C. for 18 h. The mixture was diluted with EtOAc (25 mL) and washed with water (15 mL) and brine (15 mL). Drying (MgSO4), filtration, and concentration was followed by purification (SiO2, 0-30% EtOAc in hexanes) to afford the title compound (0.056 g, 62%) as a white solid: 1H NMR (400 MHz, DMSO-d6) δ 8.34 (d, J=8.8 Hz, 1H), 8.29 (d, J=8.8 Hz, 1H) 8.23 (s, 1H), 8.09-8.06 (m, 2H), 7.83 (t, J=7.8 Hz, 1H), 7.48 (s, 1H), 6.03 (s, 2H); MS m/z 527 (M+Na).

Workup

washwashed with water (15 mL) and brine (15 mL)
customDrying
filtration(MgSO4), filtration, and concentration
customwas followed by purification (SiO2, 0-30% EtOAc in hexanes)

Sources & evidence

ORD record: ord-e00cca1a44824402ae9c5c79c5a3e7f5
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026262B2

Reaction notes

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