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Cesium carbonate → tert-butyl N-[(3S)-1-(6-bromo-4-methyl-3-oxo-pyrazin-2-yl)-3-piperidyl]carbamate

HRID 57955
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HRID 57955 반응식
Br[C:2]1[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=[C:6]([Br:8])[N:7]=1.[NH:11]1[CH2:16][CH2:15][CH2:14][C@H:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:23])([CH3:22])[CH3:21])[CH2:12]1.C(=O)([O-])[O-].[Cs+].[Cs+].CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2>O1CCOCC1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[Br:8][C:6]1[N:7]=[C:2]([N:11]2[CH2:16][CH2:15][CH2:14][C@H:13]([NH:17][C:18](=[O:24])[O:19][C:20]([CH3:22])([CH3:21])[CH3:23])[CH2:12]2)[C:3](=[O:10])[N:4]([CH3:9])[CH:5]=1
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참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 1514171tert-butyl N-[(3S)-piperidin-3-yl]carbamateHCID 130629693,5-Dibromo-1-methyl-1H-pyrazin-2-one

생성물 1

HCID 86707139tert-butyl N-[(3S)-1-(6-bromo-4-methyl-3-oxo-pyrazin-2-yl)-3-piperidyl]carbamate수율 58%

시약·촉매·용매 2

HCID 9811564Bis(dibenzylideneacetone)palladium촉매HCID 312751,4-Dioxane용매

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온도
110 °C

실험 절차

A mixture of 3,5-dibromo-1-methyl-pyrazin-2-one (2.025 mmol; 542.4 mg), tert-butyl N-[(3S)-3-piperidyl]carbamate (2.025 mmol; 405.5 mg), cesium carbonate (4.049 mmol; 1319 mg), Xantphos (0.1721 mmol; 102.7 mg), and tris(dibenzylideneacetone)dipalladium(0) (0.1012 mmol; 93.63 mg) in 1,4-dioxane (10 mL) was purged with Argon, then sealed and stirred at 110° C. overnight. The mixture was cooled to room temperature and filtered through Celite. The filtrate was concentrated and the residue was purified on silica eluted with 0 to 20% EtOAc in DCM to afford tert-butyl N-[(3S)-1-(6-bromo-4-methyl-3-oxo-pyrazin-2-yl)-3-piperidyl]carbamate as a yellow solid (451.0 mg, 58%).

후처리

  1. customwas purged with Argon
  2. customsealed
  3. temperatureThe mixture was cooled to room temperature
  4. filtrationfiltered through Celite
  5. concentrationThe filtrate was concentrated
  6. customthe residue was purified on silica
  7. washeluted with 0 to 20% EtOAc in DCM

출처 및 근거

ORD 기록
ord-0a71d5f08abc4687828e33cf2da6af07
출처 데이터셋
uspto-grants-2016_09
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US09434725B2

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