1,4-Dibromobenzene → 4-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]phenylboronic acid

HRID 1059132

반응식

HRID 1059132 반응식
Br[C:2]1[CH:7]=[CH:6][C:5](Br)=[CH:4][CH:3]=1.C([Li])CCC.[CH3:14][CH:15]([CH3:42])[C:16]([C:18]1[N:19]=[CH:20][N:21]([C:23]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=1)=[O:17].[B:43](OC)([O:46]C)[O:44]C.[Cl-].[NH4+]>C1COCC1.CCCCCC>[OH:17][C:16]([C:2]1[CH:7]=[CH:6][C:5]([B:43]([OH:46])[OH:44])=[CH:4][CH:3]=1)([C:18]1[N:19]=[CH:20][N:21]([C:23]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[CH:22]=1)[CH:15]([CH3:42])[CH3:14]

참가 물질

8

반응물 5

HCID 78041,4-DibromobenzeneHCID 8470Trimethyl borateHCID 25517Ammonium ChlorideHCID 10150490isopropyl(1-trityl-1H-imidazol-4-yl)ketoneHCID 178418339Butyllithium2회

생성물 1

HCID 186685784-[1-hydroxy-2-methyl-1-(1-trityl-1H-imidazol-4-yl)propyl]phenylboronic acid

시약·촉매·용매 2

HCID 8028Tetrahydrofuran용매2회HCID 8058Hexane용매2회

실험 절차

To a solution of p-dibromobenzene (66.0 g) in THF (700 ml) was added dropwise a solution (1.6 M; 180 ml) of n-butyllithium in hexane at —78° C., and the mixture was stirred at the same temperature for 15 min. A solution of 2-methyl-1-(1-trityl-1H-imidazol-4-yl)-1-propanone (85.0 g) in THF (250 ml) was added dropwise, and the mixture was further stirred for 15 min. To the reaction mixture was added dropwise a solution (1.6 M; 270 ml) of n-butyllithium in hexane at −78° C., and the mixture was stirred at the same temperature for 15 min, which was followed by addition of trimethyl borate (196 ml). The reaction mixture was stirred at room temperature for 2 h, and an aqueous ammonium chloride solution was added. The mixture was stirred at room temperature for 12 h, and the organic layer was separated, washed with 1N sodium hydroxide and brine and dried over anhydrous magnesium sulfate. The solvent was evaporated to give a crude product (126 g) of the title compound as an amorphous powder. This product was used in a reaction without purification.

후처리

  1. stirringthe mixture was further stirred for 15 min
  2. stirringthe mixture was stirred at the same temperature for 15 min
  3. stirringThe reaction mixture was stirred at room temperature for 2 h
  4. stirringThe mixture was stirred at room temperature for 12 h
  5. customthe organic layer was separated
  6. washwashed with 1N sodium hydroxide and brine
  7. dry with materialdried over anhydrous magnesium sulfate
  8. customThe solvent was evaporated

출처 및 근거

ORD 기록
ord-f01ae4c47fd942f59dbb22b21f6a766f
출처 데이터셋
uspto-grants-2003_02
특허 번호
US06518257B1

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