Sodium Carbonate → {4-[2-(Benzyloxy)phenyl]-1,3-thiazol-2-yl}methanol

HRID 1257466노트

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HRID 1257466 반응식
Br[C:2]1[N:3]=[C:4]([CH2:7][OH:8])[S:5][CH:6]=1.[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1B(O)O)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1.C(=O)([O-])[O-].[Na+].[Na+]>COCCOC.C(O)C>[CH2:9]([O:16][C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][C:18]=1[C:2]1[N:3]=[C:4]([CH2:7][OH:8])[S:5][CH:6]=1)[C:10]1[CH:15]=[CH:14][CH:13]=[CH:12][CH:11]=1

참가 물질

5

반응물 3

HCID 10340Sodium CarbonateHCID 2773253(2-(Benzyloxy)phenyl)boronic acidHCID 11041630(4-Bromo-1,3-thiazol-2-yl)methanol

생성물 1

HCID 58127962{4-[2-(Benzyloxy)phenyl]-1,3-thiazol-2-yl}methanol수율 88%

시약·촉매·용매 1

HCID 20074477Dimethoxyethane ethanol용매

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온도
90 °C

실험 절차

To a mixed solution of the compound (900 mg, 4.6 mmol) obtained in Example 30a, 2-benzyloxyphenylboronic acid (1.3 g, 5.6 mmol) and 2M aqueous sodium carbonate solution (2.8 mL, 5.6 mmol) in 1,2-dimethoxyethane-ethanol (v/v=3/1, 12 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (380 mg, 0.46 mmol), and the mixture was stirred at 90° C. overnight. The resulting salt was filtered and removed, and the solvent was evaporated under reduced pressure. The obtained crude product was purified by column chromatography (hexane-hexane/ethyl acetate=60/40) to give the title compound (1.2 g, 88%) as colorless crystals.

후처리

  1. filtrationThe resulting salt was filtered
  2. customremoved
  3. customthe solvent was evaporated under reduced pressure
  4. customThe obtained crude product
  5. customwas purified by column chromatography (hexane-hexane/ethyl acetate=60/40)

출처 및 근거

ORD 기록
ord-56a7a59b894a44d3bd71a45abb9efdcf
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461348B2

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