Sodium hydride → 4-Bromo-1-{2-(trityloxy)ethyl}-1H-imidazole

HRID 2277498노트

반응식

HRID 2277498 반응식
[Br:1][C:2]1[NH:6][CH:5]=[N:4][CH:3]=1.[H-].[Na+].Br[CH2:10][CH2:11][O:12][C:13]([C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1)([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=1)[C:14]1[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=1>CN(C=O)C.O>[Br:1][C:2]1[N:6]=[CH:5][N:4]([CH2:10][CH2:11][O:12][C:13]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=2)[C:26]2[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=2)[CH:3]=1

참가 물질

6

반응물 3

HCID 24758Sodium hydrideHCID 961251H-Imidazole, 4-bromo-HCID 109595312-Bromoethyl trityl ether

생성물 1

HCID 693507044-Bromo-1-{2-(trityloxy)ethyl}-1H-imidazole수율 69%

시약·촉매·용매 2

HCID 962Water용매HCID 6228Dimethylformamide용매2회

실험 절차

To a solution of 5-bromo-1H-imidazole as prepared in part A (2.2 g, 15 mmol) in DMF (22 mL) at 0° C. was added NaH (658 mg, 60% dispersion, 2.42 mmol) in small portions. The resulting solution was allowed to warm to r.t. and then stirred for 1 hr. The solution was cooled to 0° C. and 1,1′,1″-[(2-bromoethoxy)methanetriyl]tribenzene (5.5 g, 15 mmol) in DMF (10 mL) was added drop-wise. The resulting solution was allowed to warm to r.t. where stirring continued until the reaction was judged complete by TLC (16 hr). The suspension was diluted with water and extracted with DCM (2×50 mL). The organics were dried (MgSO4), filtered, and concentrated to a solid that was recrystallized (EtOAc/Hex) to give 4.47 g of the title compound (69%).

후처리

  1. temperatureThe solution was cooled to 0° C.
  2. temperatureto warm to r.t. where
  3. stirringstirring
  4. customwas judged complete by TLC (16 hr)
  5. extractionextracted with DCM (2×50 mL)
  6. dry with materialThe organics were dried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated to a solid
  9. customthat was recrystallized (EtOAc/Hex)

출처 및 근거

ORD 기록
ord-0d07b7590e494ced8a0450ef71f6a459
출처 데이터셋
uspto-grants-2015_09
특허 번호
US09133166B2

반응 노트

불러오는 중…