Sodium Iodide → Methyl-4-({4-[2-(benzyloxy)phenyl]-1,3-thiazol-2-yl}methyl)benzoate

HRID 1257467노트

반응식

HRID 1257467 반응식
[CH2:1]([O:8][C:9]1[CH:14]=[CH:13][CH:12]=[CH:11][C:10]=1[C:15]1[N:16]=[C:17]([CH2:20]O)[S:18][CH:19]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.C(N(CC)CC)C.CS(Cl)(=O)=O.[I-].[Na+].[CH3:36][O:37][C:38]([C:40]1[CH:45]=[CH:44][C:43](B(O)O)=[CH:42][CH:41]=1)=[O:39].C(=O)([O-])[O-].[Na+].[Na+]>O1CCCC1.CC(C)=O.COCCOC.C(O)C.O>[CH3:36][O:37][C:38](=[O:39])[C:40]1[CH:45]=[CH:44][C:43]([CH2:20][C:17]2[S:18][CH:19]=[C:15]([C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[O:8][CH2:1][C:2]3[CH:3]=[CH:4][CH:5]=[CH:6][CH:7]=3)[N:16]=2)=[CH:42][CH:41]=1

참가 물질

11

반응물 6

HCID 5238Sodium IodideHCID 8471TriethylamineHCID 10340Sodium CarbonateHCID 31297Methanesulfonyl chlorideHCID 27343694-Methoxycarbonylphenylboronic acidHCID 58127962{4-[2-(Benzyloxy)phenyl]-1,3-thiazol-2-yl}methanol

생성물 1

HCID 58127863Methyl-4-({4-[2-(benzyloxy)phenyl]-1,3-thiazol-2-yl}methyl)benzoate수율 21.7%

시약·촉매·용매 4

HCID 180Acetone용매HCID 962Water용매HCID 8028Tetrahydrofuran용매HCID 20074477Dimethoxyethane ethanol용매

실험 절차

To a solution (8 mL) of the compound (1.2 g, 4.0 mmol) obtained in Example 191a in tetrahydrofuran were added triethylamine (0.73 mL, 5.3 mmol) and methanesulfonylchloride (0.38 mL, 4.8 mmol), and the mixture was stirred at room temperature for 3 hr. The resulting salt was filtered and removed, and the solvent was evaporated under reduced pressure. To a solution (40 mL) of the residue in acetone was added sodium iodide (1.8 g, 12 mmol), and the mixture was stirred at room temperature overnight. Water was added to the reaction mixture, the mixture was extracted with ethyl acetate, and the solvent was evaporated under reduced pressure. To a mixed solution of the residue, 4-methoxycarbonylphenylboronic acid (870 mg, 4.8 mmol) and 2M aqueous sodium carbonate solution (2.4 mL, 4.8 mmol) in 1,2-dimethoxyethane/ethanol (v/v=3/1, 12 mL) was added [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II) dichloromethane complex (330 mg, 0.40 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=85/15) to give the title compound (360 mg, 21% in 3 steps) as colorless crystals.

후처리

  1. filtrationThe resulting salt was filtered
  2. customremoved
  3. customthe solvent was evaporated under reduced pressure
  4. stirringthe mixture was stirred at room temperature overnight
  5. extractionthe mixture was extracted with ethyl acetate
  6. customthe solvent was evaporated under reduced pressure
  7. stirringthe mixture was stirred at 90° C. overnight
  8. filtrationThe resulting salt was filtered
  9. customremoved
  10. customthe solvent was evaporated under reduced pressure
  11. customThe obtained crude product
  12. customwas purified by column chromatography (hexane-hexane/ethyl acetate=85/15)

출처 및 근거

ORD 기록
ord-43d33fb47d9b4f9a84517ecfd7cf0239
출처 데이터셋
uspto-grants-2013_06
특허 번호
US08461348B2

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