Dimethylformamide → HCID 58760951、化合物

HRID 1294845ノート

反応式

HRID 1294845 の反応式
[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]

参加物

5

反応物 3

HCID 6228DimethylformamideHCID 57437746HCID 57437746、化合物HCID 178418306HCID 178418306、化合物

生成物 1

HCID 58760951HCID 58760951、化合物

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

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).

後処理

  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

出典と根拠

ORDレコード
ord-4f75c1b4cbb141729824aa2fa362010f
出典データセット
uspto-grants-2007_07
特許番号
US07241788B2

反応ノート

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