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Cesium carbonate → HCID 68810823, 화합물

HRID 1790856
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HRID 1790856 반응식
[CH3:1][O:2][C:3]1[CH:29]=[CH:28][C:6]2[N:7]([C:10]3[CH:19]=[CH:18][C:17]4[C:12](=[C:13](OS(C(F)(F)F)(=O)=O)[CH:14]=[CH:15][CH:16]=4)[N:11]=3)[CH:8]=[N:9][C:5]=2[CH:4]=1.[C:30]([O:34][C:35](=[O:43])[NH:36][CH:37]1[CH2:42][CH2:41][NH:40][CH2:39][CH2:38]1)([CH3:33])([CH3:32])[CH3:31].C([O-])([O-])=O.[Cs+].[Cs+].C1C=CC(P(C2C(C3C(P(C4C=CC=CC=4)C4C=CC=CC=4)=CC=C4C=3C=CC=C4)=C3C(C=CC=C3)=CC=2)C2C=CC=CC=2)=CC=1>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]>[C:30]([O:34][C:35](=[O:43])[NH:36][CH:37]1[CH2:42][CH2:41][N:40]([C:17]2[CH:16]=[CH:15][CH:14]=[C:13]3[C:12]=2[N:11]=[C:10]([N:7]2[C:6]4[CH:28]=[CH:29][C:3]([O:2][CH3:1])=[CH:4][C:5]=4[N:9]=[CH:8]2)[CH:19]=[CH:18]3)[CH2:39][CH2:38]1)([CH3:33])([CH3:31])[CH3:32]
참가 물질실험 절차후처리출처 및 근거반응 노트

참가 물질

7

반응물 4

HCID 10796Cesium carbonateHCID 634876Binap, (A+-)-HCID 7238334-(N-Boc-amino)piperidineHCID 21037680HCID 21037680, 화합물

생성물 1

HCID 68810823HCID 68810823, 화합물

시약·촉매·용매 2

HCID 9811564
Bis(dibenzylideneacetone)palladium
촉매
HCID 312751,4-Dioxane용매

실험 절차

Trifluoro-methanesulfonic acid 2-(5-methoxy-benzoimidazol-1-yl)-quinolin-8-yl ester F (15.0 9, 35.4 mmol) and piperidin-4-yl-carbamic acid tert-butyl ester (14.2 9, 70.9 mmol) were dissolved in 200 mL of dioxane under an atmosphere of dry N2. To this solution was added Cs2CO3 (16.2 g, 49.6 mmol), racemic-BINAP (1.28 9, 2.12 mMol) and tris(dibenzylideneacetone)dipalladium (0) (1.29 9, 1.41 mMol) and the reaction mixture was heated to 100° C. and reacted at this temperature overnight. The mixture was then cooled to ambient temperature, filtered, and concentrated under vacuum to give an orange foam. The foam was chromatographed on flash silica gel eluting with a gradient from ethyl acetate (EtOAc)/DCM (1:5) to EtOAc/DCM (7:3) give 12.3 g of G as a slightly yellow solid.

후처리

  1. customreacted at this temperature overnight
  2. filtrationfiltered
  3. concentrationconcentrated under vacuum
  4. customto give an orange foam
  5. customThe foam was chromatographed on flash silica gel eluting with a gradient from ethyl acetate (EtOAc)/DCM (1:5) to EtOAc/DCM (7:3)
  6. customgive 12.3 g of G as a slightly yellow solid

출처 및 근거

ORD 기록
ord-d49861d3a01e4b57b560f40d8eaa5b6e
출처 데이터셋
uspto-grants-2006_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07071337B2

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