Acetonitrile → HCID 86620729, compound

HRID 1188701Notes

Reaction equation

[F:1][C:2]([F:20])([F:19])[CH2:3][C:4]1[NH:5][C:6]2[C:11]([CH:12]=1)=[C:10]([C:13]([F:16])([F:15])[F:14])[C:9]([C:17]#[N:18])=[CH:8][CH:7]=2.C([O-])([O-])=O.[Cs+].[Cs+].[F:27][C:28]([F:47])([F:46])[C:29]1[CH:30]=[C:31]([C:39]2[O:43][N:42]=[C:41]([CH2:44]Cl)[N:40]=2)[CH:32]=[C:33]([C:35]([F:38])([F:37])[F:36])[CH:34]=1.CC#N>CCOC(C)=O>[F:47][C:28]([F:27])([F:46])[C:29]1[CH:30]=[C:31]([C:39]2[O:43][N:42]=[C:41]([CH2:44][N:5]3[C:6]4[C:11](=[C:10]([C:13]([F:16])([F:15])[F:14])[C:9]([C:17]#[N:18])=[CH:8][CH:7]=4)[CH:12]=[C:4]3[CH2:3][C:2]([F:1])([F:19])[F:20])[N:40]=2)[CH:32]=[C:33]([C:35]([F:37])([F:36])[F:38])[CH:34]=1

Participants

Conditions

Temperature: 50 °C

Procedure

A mixture of the indole (0.040 g, 0.14 mmol) from step A, Cs2CO3 (0.054 g, 0.16 mmol), 5-[3,5-bis(trifluoromethyl)phenyl]-3-(chloromethyl)-1,2,4-oxadiazole (0.091 g, 0.27 mmol) and CH3CN (4 mL) was stirred at 50° C. for 24 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 (0.015 g, 19%) as an off-white solid: 1H NMR (400 MHz, CDCl3) δ 8.48 (s, 2H), 8.10 (s, 1H), 7.80 (d, J=8.6 Hz, 1H), 7.65 (d, J=8.6 Hz, 1H), 6.96 (s, 1H), 5.58 (s, 2H), 3.94 (q, 2H); MS m/z 585 (M−H).

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-ef2845c6116b40bc80a379f72a9842bd
Source dataset: uspto-grants-2014_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08673948B2

Reaction notes

Loading…