Triphenylphosphine → 2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-2,6-difluorobenzylthio)-5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole

HRID 83842노트

반응식

HRID 83842 반응식
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]([C:11]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:14]([SH:23])=[N:13][CH:12]=2)([CH3:10])[CH3:9])=[CH:4][C:3]=1[O:24][CH3:25].[Si:26]([O:33][CH2:34][CH2:35][O:36][C:37]1[CH:42]=[C:41]([F:43])[C:40]([CH2:44]O)=[C:39]([F:46])[CH:38]=1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.CC(OC(/N=N/C(OC(C)C)=O)=O)C>C1COCC1>[Si:26]([O:33][CH2:34][CH2:35][O:36][C:37]1[CH:38]=[C:39]([F:46])[C:40]([CH2:44][S:23][C:14]2[N:15]([C:16]3[CH:21]=[CH:20][C:19]([F:22])=[CH:18][CH:17]=3)[C:11]([C:8]([C:5]3[CH:6]=[CH:7][C:2]([Cl:1])=[C:3]([O:24][CH3:25])[CH:4]=3)([CH3:10])[CH3:9])=[CH:12][N:13]=2)=[C:41]([F:43])[CH:42]=1)([C:29]([CH3:32])([CH3:31])[CH3:30])([CH3:28])[CH3:27]

참가 물질

6

반응물 4

HCID 11776TriphenylphosphineHCID 5363146Diisopropyl azodicarboxylateHCID 66740670(4-(2-(Tert-butyldimethylsilyloxy)ethoxy)-2,6-difluorophenyl)methanolHCID 1784900045-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol

생성물 1

HCID 667406352-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-2,6-difluorobenzylthio)-5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole수율 66%

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

실험 절차

To a mixture of 5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole-2-thiol (136 mg, 0.36 mmol, 1.0 eq), (4-(2-(tert-butyldimethylsilyloxy)ethoxy)-2,6-difluorophenyl)methanol (115 mg, 0.36 mmol, 1.0 eq) and triphenylphosphine (140 mg, 0.54 mmol, 1.5 eq) in dry THF (2 mL) was added diisopropylazodicarboxylate (0.1 mL). After stirring 16 h, the reaction mixture was concentrated and purified by chromatography (silica, 0-50% EtOAc/Hex) to afford 2-(4-(2-(tert-butyldimethylsilyloxy)ethoxy)-2,6-difluorobenzylthio)-5-(2-(4-chloro-3-methoxyphenyl)propan-2-yl)-1-(4-fluorophenyl)-1H-imidazole (161 mg, 66%). 1H NMR (400 MHz, CDCl3) δ 7.56 (s, 1H), 7.11 (d, J=7.9 Hz, 1H), 6.76 (dd, J=8.9, 7.8 Hz, 2H), 6.39-6.23 (m, 6H), 4.61 (s, 2H), 3.94-3.80 (m, 4H), 3.69 (s, 3H), 1.45 (s, 6H), 1.26-1.15 (m, 3H), 0.81 (s, 9H), 0.00 (s, 6H).

후처리

  1. concentrationthe reaction mixture was concentrated
  2. custompurified by chromatography (silica, 0-50% EtOAc/Hex)

출처 및 근거

ORD 기록
ord-0e8c829c3b2947d09cadca4073c21877
출처 데이터셋
uspto-grants-2014_09
특허 번호
US08846739B2

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