Cesium carbonate → Tert-butyl 4-(1-{[6-(trifluoromethyl)pyridin-2-yl]thio}ethyl)piperidine-1-carboxylate

HRID 1873848노트

반응식

HRID 1873848 반응식
[SH:1][CH:2]([CH:4]1[CH2:9][CH2:8][N:7]([C:10]([O:12][C:13]([CH3:16])([CH3:15])[CH3:14])=[O:11])[CH2:6][CH2:5]1)[CH3:3].Br[C:18]1[CH:23]=[CH:22][CH:21]=[C:20]([C:24]([F:27])([F:26])[F:25])[N:19]=1.C([O-])([O-])=O.[Cs+].[Cs+]>C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1(C)C=CC=CC=1>[F:25][C:24]([F:27])([F:26])[C:20]1[N:19]=[C:18]([S:1][CH:2]([CH:4]2[CH2:5][CH2:6][N:7]([C:10]([O:12][C:13]([CH3:15])([CH3:14])[CH3:16])=[O:11])[CH2:8][CH2:9]2)[CH3:3])[CH:23]=[CH:22][CH:21]=1

참가 물질

6

반응물 3

HCID 10796Cesium carbonateHCID 27829022-Bromo-6-(trifluoromethyl)pyridineHCID 59447341tert-Butyl 4-(1-mercaptoethyl)piperidine-1-carboxylate

생성물 1

HCID 59447422Tert-butyl 4-(1-{[6-(trifluoromethyl)pyridin-2-yl]thio}ethyl)piperidine-1-carboxylate수율 94.2%

시약·촉매·용매 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)촉매HCID 1140Toluene용매

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온도
75 °C

실험 절차

To a 16 ml vial was added tert-butyl 4-(1-mercaptoethyl)piperidine-1-carboxylate (500 mg, 2.04 mmol), 2-bromo-6-(trifluoromethyl)pyridine (460 mg, 2.04 mmol), Pd(dppf)Cl2 (42 mg, 0.051 mmol) and Cs2CO3 (996 mg, 3.06 mmol) and 4 ml toluene. The vial was flushed with nitrogen, sealed and heated at 75° C. for 36 hours. After cooling to room temperature, the reaction mixture was diluted with 30 ml ether, and washed with 30 ml water. The organics were dried over sodium sulfate, filtered and concentrated. The residue was purified on silica gel column eluted with 1:9 to 1:4 ethyl acetate/hexane to give 750 mg desired product was light yellow oil.

후처리

  1. customThe vial was flushed with nitrogen
  2. customsealed
  3. temperatureAfter cooling to room temperature
  4. additionthe reaction mixture was diluted with 30 ml ether
  5. washwashed with 30 ml water
  6. dry with materialThe organics were dried over sodium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated
  9. customThe residue was purified on silica gel column
  10. washeluted with 1:9 to 1:4 ethyl acetate/hexane

출처 및 근거

ORD 기록
ord-6959e05b06894ce2ae505021ec0458a0
출처 데이터셋
uspto-grants-2012_11
특허 번호
US08304434B2

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