Cesium carbonate → (2-Methyl-4-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy]-phenylsulfanyl)-acetic acid tert-butyl ester

HRID 1242310노트

반응식

HRID 1242310 반응식
Cl[CH:2]([C:4]1[C:5]([CH3:20])=[N:6][C:7]([C:10]2[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=2)=[CH:8][CH:9]=1)[CH3:3].[C:21]([O:25][C:26](=[O:37])[CH2:27][S:28][C:29]1[CH:34]=[CH:33][C:32]([OH:35])=[CH:31][C:30]=1[CH3:36])([CH3:24])([CH3:23])[CH3:22].C([O-])([O-])=O.[Cs+].[Cs+]>CC(C)=O>[C:21]([O:25][C:26](=[O:37])[CH2:27][S:28][C:29]1[CH:34]=[CH:33][C:32]([O:35][CH:2]([C:4]2[C:5]([CH3:20])=[N:6][C:7]([C:10]3[CH:15]=[CH:14][C:13]([C:16]([F:19])([F:18])[F:17])=[CH:12][CH:11]=3)=[CH:8][CH:9]=2)[CH3:3])=[CH:31][C:30]=1[CH3:36])([CH3:24])([CH3:23])[CH3:22]

참가 물질

5

반응물 3

HCID 10796Cesium carbonateHCID 21935947[Rac]-3-(1-chloro-ethyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridineHCID 67072245(4-Hydroxy-2-methyl-phenylsulfanyl)-acetic acid tert-butyl ester

생성물 1

HCID 69526547(2-Methyl-4-{1-[2-methyl-6-(4-trifluoromethyl-phenyl)-pyridin-3-yl]-ethoxy]-phenylsulfanyl)-acetic acid tert-butyl ester

시약·촉매·용매 1

HCID 180Acetone용매

실험 절차

To 0.118 g (0.39 mmol) of the above prepared [rac]-3-(1-chloro-ethyl)-2-methyl-6-(4-trifluoromethyl-phenyl)-pyridine (example 17C]) and 0.100 g (0.39 mmol) of (4-hydroxy-2-methyl-phenylsulfanyl)-acetic acid tert-butyl ester (see below example 20C]), dissolved in 2.0 ml of abs. acetone, were added successively 0.065 g (0.39 mmol) of KI and 0.154 g (0.47 mmol) of Cs2CO3. The reaction was allowed to proceed for 2 h at ambient temperature, when TLC still indicated large amounts of starting material. Therefore, stirring was continued over night at 40° C. Pouring onto crashed ice, extraction with AcOEt, filtration over Celite, washing of the organic layer with water, drying over sodium sulfate, and evaporation of the solvents, followed by flash chromatography (SiO2, hexane/AcOEt=9/1), produced 0.143 g of the title compound as colorless oil.

후처리

  1. dissolutiondissolved in 2.0 ml of abs
  2. waitwas continued over night at 40° C
  3. additionPouring
  4. extractionice, extraction
  5. filtrationwith AcOEt, filtration over Celite
  6. washwashing of the organic layer with water
  7. dry with materialdrying over sodium sulfate, and evaporation of the solvents

출처 및 근거

ORD 기록
ord-7ed52eb9620043329d78ba5c5dddc03c
출처 데이터셋
uspto-grants-2006_10
특허 번호
US07115611B2

반응 노트

불러오는 중…