Triisopropyl borate → {3-[Bis(4-methoxybenzyl)amino]-4-chlorophenyl}boronic acid

HRID 1476060노트

반응식

HRID 1476060 반응식
C([Li])CCC.Br[C:7]1[CH:8]=[CH:9][C:10]([Cl:32])=[C:11]([CH:31]=1)[N:12]([CH2:22][C:23]1[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=1)[CH2:13][C:14]1[CH:19]=[CH:18][C:17]([O:20][CH3:21])=[CH:16][CH:15]=1.[B:33](OC(C)C)([O:38]C(C)C)[O:34]C(C)C>CCCCCC.C1COCC1.C(OCC)C>[CH3:21][O:20][C:17]1[CH:18]=[CH:19][C:14]([CH2:13][N:12]([CH2:22][C:23]2[CH:28]=[CH:27][C:26]([O:29][CH3:30])=[CH:25][CH:24]=2)[C:11]2[CH:31]=[C:7]([B:33]([OH:38])[OH:34])[CH:8]=[CH:9][C:10]=2[Cl:32])=[CH:15][CH:16]=1

참가 물질

6

반응물 3

HCID 21531Triisopropyl borateHCID 58288251HCID 58288251, 화합물HCID 178418339Butyllithium

생성물 1

HCID 58288209{3-[Bis(4-methoxybenzyl)amino]-4-chlorophenyl}boronic acid

시약·촉매·용매 2

HCID 8058Hexane용매HCID 21868444Ether tetrahydrofuran용매

반응 조건

온도
-78 °C

실험 절차

Under argon and at −78° C., 6.1 ml (15.25 mmol) of a 2.5 M solution of n-butyllithium in hexane were slowly added dropwise to a solution of 5.2 g (11.64 mmol) of 5-bromo-2-chloro-N,N-bis(4-methoxybenzyl)aniline in 100 ml of THF/diethyl ether (1:1). The reaction solution was stirred at −78° C. for 60 min, and 4.3 ml (18.62 mmol) of triisopropyl borate were then added slowly. The reaction solution was then stirred at −78° C. for another 15 min, then slowly warmed to room temperature and stirred at this temperature for another 3 h. 150 ml of ice-water were then metered in. The organic phase was separated off, and the aqueous phase was then extracted three more times with ethyl acetate. The combined organic phases were dried over sodium sulphate. After filtration, the solvent was removed under reduced pressure. The crude product was purified chromatographically on silica gel (mobile phase: initially cyclohexane/ethyl acetate 10:1→9:1→4:1, then dichloromethane/methanol 95:5). This gave 2.54 g (6.17 mmol, 53% of theory) of the title compound.

후처리

  1. stirringThe reaction solution was then stirred at −78° C. for another 15 min
  2. temperatureslowly warmed to room temperature
  3. stirringstirred at this temperature for another 3 h
  4. customThe organic phase was separated off
  5. extractionthe aqueous phase was then extracted three more times with ethyl acetate
  6. dry with materialThe combined organic phases were dried over sodium sulphate
  7. filtrationAfter filtration
  8. customthe solvent was removed under reduced pressure
  9. customThe crude product was purified chromatographically on silica gel (mobile phase

출처 및 근거

ORD 기록
ord-92a411c092cb46f0848c9aa8183e5310
출처 데이터셋
uspto-grants-2015_04
특허 번호
US09018414B2

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