Furan-3-boronic acid → 4-(3-Chloro-phenylethynyl)-1-furan-3-yl-2-methyl-1H-imidazole

HRID 1294491

반응식

HRID 1294491 반응식
[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:15])[NH:13][CH:14]=2)[CH:5]=[CH:6][CH:7]=1.[O:16]1[CH:20]=[CH:19][C:18](B(O)O)=[CH:17]1>ClCCl>[Cl:1][C:2]1[CH:3]=[C:4]([C:8]#[C:9][C:10]2[N:11]=[C:12]([CH3:15])[N:13]([C:18]3[CH:19]=[CH:20][O:16][CH:17]=3)[CH:14]=2)[CH:5]=[CH:6][CH:7]=1

참가 물질

4

반응물 2

HCID 2734358Furan-3-boronic acidHCID 178432693HCID 178432693, 화합물

생성물 1

HCID 668795994-(3-Chloro-phenylethynyl)-1-furan-3-yl-2-methyl-1H-imidazole

시약·촉매·용매 1

HCID 6344Dichloromethane용매

실험 절차

4-(3-Chloro-phenylethynyl)-2-methyl-1H-imidazole (200 mg, 0.92 mmol) was dissolved in 10 mL dichloromethane. Powdered molecular sieves (3 A, 200 mg), 3-furaneboronic acid (207 mg, 1.85 mmol) and [Cu(OH)TMEDA]2Cl2 (43 mg, 0.093 mmol) were added. Oxygen was bubbled through the reaction mixture for 10 minutes and stirring was continued at room temperature overnight. The reaction mixture was filtered through a dicalite speed plus pad and washed with 50 mL dichloromethane. The filtrate was washed with 50 mL water, dried with magnesium sulfate, filtered and evaporated. The crude product was purified by flash chromatography on silica gel (dichloromethane/methanol 100:0->90:10 gradient) and the desired compound was as a brown oil (21 mg, 8%), MS: m/e=283.1 (M+H+).

후처리

  1. customOxygen was bubbled through the reaction mixture for 10 minutes
  2. filtrationThe reaction mixture was filtered through a dicalite speed plus pad
  3. washwashed with 50 mL dichloromethane
  4. washThe filtrate was washed with 50 mL water
  5. dry with materialdried with magnesium sulfate
  6. filtrationfiltered
  7. customevaporated
  8. customThe crude product was purified by flash chromatography on silica gel (dichloromethane/methanol 100:0->90:10 gradient)

출처 및 근거

ORD 기록
ord-90ea6191f94d4d1b9dd601134cd6cfc3
출처 데이터셋
uspto-grants-2007_07
특허 번호
US07241760B2

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