2,5-Dihydrofuran → (1H-benzo[d]imidazol-2-yl)(4-(3-(2,3-dihydro furan-3-yl)pyridin-2-yloxy)phenyl)methanone

HRID 410292노트

반응식

HRID 410292 반응식
[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24](Br)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11].[O:26]1[CH2:30][CH:29]=[CH:28][CH2:27]1.C1(N(C)C2CCCCC2)CCCCC1>O1CCOCC1.CCOC(C)=O.CC(C)([P](C(C)(C)C)([Pd][P](C(C)(C)C)(C(C)(C)C)C(C)(C)C)C(C)(C)C)C>[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([CH:30]3[CH2:29][CH:28]=[CH:27][O:26]3)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11].[NH:1]1[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=2[N:3]=[C:2]1[C:10]([C:12]1[CH:17]=[CH:16][C:15]([O:18][C:19]2[C:24]([CH:29]3[CH:28]=[CH:27][O:26][CH2:30]3)=[CH:23][CH:22]=[CH:21][N:20]=2)=[CH:14][CH:13]=1)=[O:11]

참가 물질

8

반응물 3

HCID 155702,5-DihydrofuranHCID 24210N-Methyl dicyclohexylamineHCID 59326957(1H-benzo[d]imidazol-2-yl)(4-(3-bromopyridin-2-yloxy)phenyl)methanone

생성물 2

HCID 59326803(1H-benzo[d]imidazol-2-yl)(4-(3-(2,3-dihydro furan-3-yl)pyridin-2-yloxy)phenyl)methanoneHCID 59327153(1H-benzo[d]imidazol-2-yl)(4-(3-(2,3-dihydrofuran-2-yl)pyridin-2-yloxy)phenyl)methanone

시약·촉매·용매 3

HCID 178418851HCID 178418851, 화합물촉매HCID 8857Ethyl Acetate용매HCID 312751,4-Dioxane용매

반응 조건

온도
80 °C

실험 절차

A mixture of (1H-benzo[d]imidazol-2-yl)(4-(3-bromopyridin-2-yloxy)phenyl)methanone (1.522 g, 3.86 mmol), 2,5-dihydrofuran (1.400 mL, 18.98 mmol, Aldrich), N-cyclohexyl-N-methylcyclohexanamine (1.600 mL, 7.54 mmol, Aldrich) and bis(tri-tert-butylphosphine)palladium (0) (0.194 g, 0.380 mmol, Strem) in dioxane (10 mL) was sealed in a microwave vessel under an atmosphere of argon and heated thermally at 80° C. for 6 h. The reaction was diluted with EtOAc and the mixture was extracted with water (1×) and brine (1×). The organic mixture was evaporated onto silica gel and purified by flash chromatography (Isco (120 gram)) eluting with EtOAc:hexanes (0:1→1:2) to give 650 mg of (1H-benzo[d]imidazol-2-yl)(4-(3-(2,3-dihydrofuran-2-yl)pyridin-2-yloxy)phenyl)methanone and 325 mg of (1H-benzo[d]imidazol-2-yl)(4-(3-(2,3-dihydro furan-3-yl)pyridin-2-yloxy)phenyl)methanone.

후처리

  1. customwas sealed in a microwave vessel under an atmosphere of argon
  2. extractionthe mixture was extracted with water (1×) and brine (1×)
  3. customThe organic mixture was evaporated onto silica gel
  4. custompurified by flash chromatography (Isco (120 gram))
  5. washeluting with EtOAc:hexanes (0:1→1:2)

출처 및 근거

ORD 기록
ord-ae7d634543124ef5bb91d81aeaf0ab07
출처 데이터셋
uspto-grants-2014_06
특허 번호
US08759532B2

반응 노트

불러오는 중…