Acetonitrile → HCID 86620729, compound

HRID 913773Notes

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-25f2f08227c543f49ef1c1b74f0238a8
Source dataset: uspto-grants-2011_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08026262B2

Reaction notes

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