Dimethylformamide → HCID 58760951, 화합물

HRID 1766416노트

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HRID 1766416 반응식
[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[N:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:10]=1Br)=[O:5])[CH3:2].C([Li])(C)(C)C.CN([CH:34]=[O:35])C>C1COCC1>[CH2:1]([O:3][C:4]([C:6]1[N:7]=[C:8]([C:19]2[CH:24]=[CH:23][CH:22]=[CH:21][C:20]=2[Cl:25])[N:9]([C:12]2[CH:17]=[CH:16][C:15]([Cl:18])=[CH:14][CH:13]=2)[C:10]=1[CH:34]=[O:35])=[O:5])[CH3:2]

참가 물질

5

반응물 3

HCID 6228DimethylformamideHCID 57437746HCID 57437746, 화합물HCID 178418306HCID 178418306, 화합물

생성물 1

HCID 58760951HCID 58760951, 화합물

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

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온도
-78 °C

실험 절차

To a solution of 5-bromo-1-(4-chloro-phenyl)-2-(2-chloro-phenyl)-1H-imidazole-4-carboxylic acid ethyl ester (I-5d, 4.4 g, 0.01 mmol) in anhydrous THF (100 ml) and under a N2 atmosphere at −78° C. was slowly added tert.-butyl lithium (13 ml of 1.7 M solution in pentane, 0.22 mol). After 1 hour at −78° C., DMF (7.7 ml, 0.1 mmol) was added dropwise. The reaction mixture was stirred at −78° C. for 2.5 hours, quenched with sat'd aq. NH4Cl (10 ml), allowed to slowly warm to room temperature, and finally poured into sat'd aq. NaCl. The aqueous solution was extracted with Et2O (3×) and the combined organic extracts were dried (Na2SO4) and concentrated in vacuo. The crude residue was purified via flash chromatography using a solvent gradient of 1:3 EtOAc/hexanes to 1:1 EtOAc/hexanes to give the desired product I-5e as a pale yellow amorphous glass (2.0 g): +APCI MS (M+1) 389.2; 1H NMR (CD2Cl2) δ 1.41 (3H, t), 4.45 (2H, q), 7.09-7.14 (2H, m), 7.24-7.39 (7H, m), 10.50 (1H, s).

후처리

  1. customat −78° C.
  2. customquenched with sat'd aq. NH4Cl (10 ml)
  3. temperatureto slowly warm to room temperature
  4. additionfinally poured into sat'd aq. NaCl
  5. extractionThe aqueous solution was extracted with Et2O (3×)
  6. dry with materialthe combined organic extracts were dried (Na2SO4)
  7. concentrationconcentrated in vacuo
  8. customThe crude residue was purified via flash chromatography

출처 및 근거

ORD 기록
ord-3eb4b78a10954d128463963e1cb53f00
출처 데이터셋
uspto-grants-2007_06
특허 번호
US07230024B2

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