4-Chloro-3-(trifluoromethyl)benzoic acid → HCID 24984142, compound

HRID 2102061Notes

Reaction equation

HRID 2102061 reaction equation
[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]([OH:8])=O)=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12].[C:15]([C:17]1[C:18]([C:31]([F:34])([F:33])[F:32])=[C:19]2[C:23](=[CH:24][CH:25]=1)[N:22]([CH2:26][C:27](=[NH:30])[NH:28]O)[CH:21]=[CH:20]2)#[N:16]>CC#N>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[O:8][N:30]=[C:27]([CH2:26][N:22]3[C:23]4[C:19](=[C:18]([C:31]([F:34])([F:32])[F:33])[C:17]([C:15]#[N:16])=[CH:25][CH:24]=4)[CH:20]=[CH:21]3)[N:28]=2)=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12]

Participants

4

Reactant 2

HCID 27738574-Chloro-3-(trifluoromethyl)benzoic acidHCID 178509476HCID 178509476, compound

Product 1

HCID 24984142HCID 24984142, compoundYield 65.5%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

To 4-chloro-3-(trifluoromethyl)benzoic acid (0.0159 g, 0.071 mmol) in CH3CN (3 mL) was added CDl (0.0115 g, 0.071 mmol) and the resulting mixture was stirred for 5 min at rt. Next, 2-[5-cyano-4-(trifluoromethyl)-1H-indol-1-yl]-N-hydroxyethanimidamide (Example 64) (0.02 g, 0.071 mmol) was added and the mixture was stirred for 1 h at rt. Heating at 150° C. in a microwave for 10 min was followed by direct purification (column chromatography, EtOAc/hexanes) to obtain the title compound (0.0219 g): MS (ES) m/z 471 (M+1).

Workup

  1. stirringthe mixture was stirred for 1 h at rt
  2. temperatureHeating at 150° C. in a microwave for 10 min
  3. customwas followed by direct purification (column chromatography, EtOAc/hexanes)

Sources & evidence

ORD record
ord-0daf80d3c1a245e4aa1d5f4e41c1683e
Source dataset
uspto-grants-2009_08
Patent number
US07572820B2

Reaction notes

Loading…