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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 1627324
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HRID 1627324 반응식
[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]
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참가 물질

5

반응물 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

생성물 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-fluorobenzoate수율 68.1%

시약·촉매·용매 2

HCID 345198Adams' catalyst촉매
HCID 702
Ethanol
용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-7c545cfc80ec45e39420dcaa46f7c623
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08785488B2

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