2-Fluoro-5-(trifluoromethyl)benzoic acid → 1-({5-[2-Fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-4-(trifluoromethyl)-1H-indole-5-carbonitrile

HRID 2101873Notes

Reaction equation

HRID 2101873 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]([OH:6])=O.CCN=C=NCCCN(C)C.Cl.[C:27]([C:29]1[C:30]([C:43]([F:46])([F:45])[F:44])=[C:31]2[C:35](=[CH:36][CH:37]=1)[N:34]([CH2:38][C:39](=[NH:42])[NH:40]O)[CH:33]=[CH:32]2)#[N:28]>ClCCCl>[F:1][C:2]1[CH:10]=[CH:9][C:8]([C:11]([F:14])([F:13])[F:12])=[CH:7][C:3]=1[C:4]1[O:6][N:42]=[C:39]([CH2:38][N:34]2[C:35]3[C:31](=[C:30]([C:43]([F:46])([F:44])[F:45])[C:29]([C:27]#[N:28])=[CH:37][CH:36]=3)[CH:32]=[CH:33]2)[N:40]=1

Participants

5

Reactant 3

HCID 6882922-Fluoro-5-(trifluoromethyl)benzoic acidHCID 27239391,3-Propanediamine, N'-(ethylcarbonimidoyl)-N,N-dimethyl-, monohydrochlorideHCID 178509476HCID 178509476, compound

Product 1

HCID 249839871-({5-[2-Fluoro-5-(trifluoromethyl)phenyl]-1,2,4-oxadiazol-3-yl}methyl)-4-(trifluoromethyl)-1H-indole-5-carbonitrileYield 49.6%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
80 °C

Procedure

2-Fluoro-5-(trifluoromethyl)benzoic acid (0.016 g, 0.075 mmol) and EDCl (0.015 g, 0.078 mmol) were stirred in DCE (2 mL) for 5 min at rt and then 2-[5-cyano-4-(trifluoromethyl)-1H-indol-1-yl]-N-hydroxyethanimidamide (0.020 g, 0.071 mmol) was added. After 1 h at rt, the reaction was heated to 80° C. for 15 h. Direct purification (SiO2, EtOAc/hexanes) provided the title compound (0.016 g): MS (ESI): m/z 455 (M+1).

Workup

  1. customDirect purification (SiO2, EtOAc/hexanes)

Sources & evidence

ORD record
ord-e407e61667f8401b9c260a92787042a4
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

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