Nitrogen → ethyl 3-chloro-4-(2-(5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)ethyl)-5-fluorobenzoate

HRID 83926Notes

Reaction equation

HRID 83926 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([F:39])[C:12]=1[CH:13]=[CH:14][C:15]1[N:16]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[C:17]([C:20]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([O:30][CH3:31])[CH:24]=2)([CH3:22])[CH3:21])=[CH:18][N:19]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6].N#N>CCO.O=[Pt]=O>[Cl:1][C:2]1[CH:3]=[C:4]([CH:10]=[C:11]([F:39])[C:12]=1[CH2:13][CH2:14][C:15]1[N:16]([C:32]2[CH:37]=[CH:36][C:35]([F:38])=[CH:34][CH:33]=2)[C:17]([C:20]([C:23]2[CH:28]=[CH:27][C:26]([Cl:29])=[C:25]([O:30][CH3:31])[CH:24]=2)([CH3:21])[CH3:22])=[CH:18][N:19]=1)[C:5]([O:7][CH2:8][CH3:9])=[O:6]

Participants

5

Reactant 2

HCID 947NitrogenHCID 66740361ethyl 3-chloro-4-(2-(5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)vinyl)-5-fluorobenzoate

Product 1

HCID 66739864ethyl 3-chloro-4-(2-(5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)ethyl)-5-fluorobenzoateYield 68.1%

Reagents, catalysts & solvents 2

HCID 345198Adams' catalystCatalystHCID 702EthanolSolvent

Procedure

A solution of ethyl 3-chloro-4-(2-(5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)vinyl)-5-fluorobenzoate (224 mg, 0.392 mmol) in EtOH (10 mL) was degassed using N2 for 5-10 minutes prior to the addition of PtO2 (42 mg, 0.184 mmol). The resulting suspension was pressurized with 70 psi H2 and agitated overnight. The catalyst was removed by filtration through Celite™ and eluting with more EtOH. The filtrate was concentrated in vacuo to provide ethyl 3-chloro-4-(2-(5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazol-2-yl)ethyl)-5-fluorobenzoate (153 mg, 68%) as a gray oil. 1H NMR (400 MHz, CDCl3) δ 7.87-7.61 (m, 1H), 7.50 (td, J=9.4, 1.4 Hz, 1H), 7.15 (d, J=8.4 Hz, 1H), 7.11-6.98 (m, 1H), 6.98-6.65 (m, 2H), 6.65-6.32 (m, 4H), 4.38 (dq, J=21.4, 7.1 Hz, 2H), 3.74 (d, J=3.3 Hz, 3H), 3.25-2.83 (m, 2H), 2.52 (dd, J=16.6, 8.9 Hz, 2H), 1.50 (s, 6H), 1.39 (dt, J=14.3, 7.2 Hz, 3H).

Workup

  1. customfor 5-10 minutes
  2. customThe catalyst was removed by filtration through Celite™
  3. washeluting with more EtOH
  4. concentrationThe filtrate was concentrated in vacuo

Sources & evidence

ORD record
ord-f0937de2b40f45e6bc751e7b617ab0e2
Source dataset
uspto-grants-2014_09
Patent number
US08846739B2

Reaction notes

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