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

HRID 1257466ノート

反応式

HRID 1257466 の反応式
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

参加物

5

反応物 3

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

生成物 1

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

試薬・触媒・溶媒 1

HCID 20074477Dimethoxyethane ethanol溶媒

反応条件

温度
90 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-56a7a59b894a44d3bd71a45abb9efdcf
出典データセット
uspto-grants-2013_06
特許番号
US08461348B2

反応ノート

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