1,1'-Carbonyldiimidazole → 1-{1-[3-(4-Fluorophenyl)-1,2,4-oxadiazol-5-yl]ethyl}-4-(trifluoromethyl)-1H-indole-5-carbonitrile

HRID 913642Notes

Reaction equation

HRID 913642 reaction equation
[C:1]([C:3]1[C:4]([C:17]([F:20])([F:19])[F:18])=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([CH:12]([CH3:16])[C:13]([OH:15])=O)[CH:7]=[CH:6]2)#[N:2].C1N=CN(C(N2C=NC=C2)=O)C=1.[F:33][C:34]1[CH:39]=[CH:38][C:37]([C:40](=[NH:43])[NH:41]O)=[CH:36][CH:35]=1>CC#N>[F:33][C:34]1[CH:39]=[CH:38][C:37]([C:40]2[N:43]=[C:13]([CH:12]([N:8]3[C:9]4[C:5](=[C:4]([C:17]([F:20])([F:19])[F:18])[C:3]([C:1]#[N:2])=[CH:11][CH:10]=4)[CH:6]=[CH:7]3)[CH3:16])[O:15][N:41]=2)=[CH:36][CH:35]=1

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 578000922-[5-Cyano-4-(trifluoromethyl)-1H-indol-1-yl]propanoic acidHCID 178513323HCID 178513323, compound

Product 1

HCID 578003601-{1-[3-(4-Fluorophenyl)-1,2,4-oxadiazol-5-yl]ethyl}-4-(trifluoromethyl)-1H-indole-5-carbonitrileYield 8%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 2-[5-cyano-4-(trifluoromethyl)-1H-indol-1-yl]propanoic acid (0.06 g, 0.212 mmol) in CH3CN (3 mL) was added CDI (0.034 g, 0.212 mmol). After 5 min, 4-fluoro-N-hydroxybenzenecarboximidamide (0.033 g, 0.212 mmol) was added. The resulting mixture was stirred at rt and then heated to 150° C. in a microwave for 20 min. Concentration was followed by column chromatography (EtOAc/hexanes) to obtain the desired product (0.0065 g, 8% yield): MS (APCl) m/z 401 (M+1).

Workup

  1. temperatureheated to 150° C. in a microwave for 20 min
  2. concentrationConcentration

Sources & evidence

ORD record
ord-382615523448429398ff11376caf6343
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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