1,1'-Carbonyldiimidazole → HCID 24984142, compound

HRID 913628Notes

Reaction equation

HRID 913628 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].C1N=CN(C(N2C=NC=C2)=O)C=1.[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]>CC#N>[Cl:1][C:2]1[CH:10]=[CH:9][C:5]([C:6]2[O:8][N:42]=[C:39]([CH2:38][N:34]3[C:35]4[C:31](=[C:30]([C:43]([F:46])([F:44])[F:45])[C:29]([C:27]#[N:28])=[CH:37][CH:36]=4)[CH:32]=[CH:33]3)[N:40]=2)=[CH:4][C:3]=1[C:11]([F:14])([F:13])[F:12]

Participants

5

Reactant 3

HCID 682631,1'-CarbonyldiimidazoleHCID 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 CDI (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-7d742a7f71b544d89a1005f41e739260
Source dataset
uspto-grants-2011_09
Patent number
US08026262B2

Reaction notes

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