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Triethylamine → 1-[4-(7-Ethynyl-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamine

HRID 872351
Notizen
Druckvorschau

Reaktionsgleichung

Reaktionsgleichung von HRID 872351
[C:1]1([C:7]2[N:11]3[CH:12]=[CH:13][C:14]([C:16]#[C:17][Si](C)(C)C)=[CH:15][C:10]3=[N:9][C:8]=2[C:22]2[CH:27]=[CH:26][C:25]([C:28]3([NH2:32])[CH2:31][CH2:30][CH2:29]3)=[CH:24][CH:23]=2)[CH:6]=[CH:5][CH:4]=[CH:3][CH:2]=1.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.C(N(CC)CC)C>C1COCC1>[C:16]([C:14]1[CH:13]=[CH:12][N:11]2[C:7]([C:1]3[CH:2]=[CH:3][CH:4]=[CH:5][CH:6]=3)=[C:8]([C:22]3[CH:27]=[CH:26][C:25]([C:28]4([NH2:32])[CH2:29][CH2:30][CH2:31]4)=[CH:24][CH:23]=3)[N:9]=[C:10]2[CH:15]=1)#[CH:17]
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Komponenten

5

Edukt 3

HCID 8471TriethylamineHCID 2724141Tetrabutylammonium FluorideHCID 666650621-[4-(3-Phenyl-7-trimethylsilanylethynyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamine

Produkt 1

HCID 866910431-[4-(7-Ethynyl-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamineAusbeute 47,2 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 8028
Tetrahydrofuran
Lösungsmittel
2×

Versuchsvorschrift

To a solution of 1-[4-(3-phenyl-7-trimethylsilanylethynyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamine (31 mg, 0.07 mmol) in THF (0.5 mL) was added a 1 M solution of tetra-n-butylammonium fluoride in THF (0.2 mL, 0.2 mmol, 3.0 equiv). The resulting solution was stirred at room temperature for 18 h, then was separated between water (15 mL) and EtOAc (15 mL). The aqueous layer was extracted with EtOAc (2×15 mL). The combined organic phases were washed with water (15 mL), dried (Na2SO4 anh) and concentrated under reduced pressure. The remaining material was treated with triethylamine (0.03 mL, 0.21 mmol, 3.0 equiv) and the resulting material was purified using MPLC (Biotage Isolera Flash NH2 Snap 10 reverse phase column; 100% CH2Cl2 for 8.5 min., gradient to 95% CH2Cl2: 5% MeOH over 7 min.; 95% CH2Cl2: 5% MeOH for 9 min.) to give 1-[4-(7-ethynyl-3-phenyl-imidazo[1,2-a]pyridin-2-yl)-phenyl]-cyclobutylamine (12 mg, 39%).

Aufarbeitung

  1. customwas separated between water (15 mL) and EtOAc (15 mL)
  2. extractionThe aqueous layer was extracted with EtOAc (2×15 mL)
  3. washThe combined organic phases were washed with water (15 mL)
  4. dry with materialdried (Na2SO4 anh)
  5. concentrationconcentrated under reduced pressure
  6. customthe resulting material was purified
  7. wait100% CH2Cl2 for 8.5 min.
  8. waitgradient to 95% CH2Cl2: 5% MeOH over 7 min.

Quellen und Nachweise

ORD-Eintrag
ord-9c0647213af24c89925a1b94882446ad
Quelldatensatz
uspto-grants-2015_03
DOI
10.6084/m9.figshare.5104873.v1
Patentnummer
US08975265B2

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