Dimethylformamide → 7-(Difluoromethoxy)-4-((6-(3-methylisoxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)quinoline

HRID 40333

Reaktionsgleichung

Reaktionsgleichung von HRID 40333
Cl[C:2]([F:7])([F:6])C([O-])=O.[Na+].Br.[CH3:10][C:11]1[CH:15]=[C:14]([C:16]2[CH:17]=[CH:18][C:19]3[N:20]([C:22]([CH2:25][O:26][C:27]4[C:36]5[C:31](=[CH:32][C:33]([OH:37])=[CH:34][CH:35]=5)[N:30]=[CH:29][CH:28]=4)=[N:23][N:24]=3)[CH:21]=2)[O:13][N:12]=1.C(=O)([O-])[O-].[Cs+].[Cs+].CN(C=O)C>C(O)=O>[F:7][CH:2]([F:6])[O:37][C:33]1[CH:32]=[C:31]2[C:36]([C:27]([O:26][CH2:25][C:22]3[N:20]4[CH:21]=[C:16]([C:14]5[O:13][N:12]=[C:11]([CH3:10])[CH:15]=5)[CH:17]=[CH:18][C:19]4=[N:24][N:23]=3)=[CH:28][CH:29]=[N:30]2)=[CH:35][CH:34]=1

Komponenten

6

Edukt 4

HCID 6228DimethylformamideHCID 10796Cesium carbonateHCID 2734985Sodium chlorodifluoroacetateHCID 1363872144-((6-(3-Methylisoxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)quinolin-7-ol hydrobromide

Produkt 1

HCID 576909917-(Difluoromethoxy)-4-((6-(3-methylisoxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)quinolineAusbeute 13,4 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 284Formic AcidLösungsmittel

Versuchsvorschrift

A 48 mL tube was charged with sodium 2-chloro-2,2-difluoroacetate (0.15 g, 1.0 mmol), 4-((6-(3-methylisoxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)quinolin-7-ol hydrobromide (0.200 g, 0.44 mmol), cesium carbonate (0.43 g, 1.3 mmol), and DMF (1.7 ml, 22 mmol), flushed with argon, sealed, then placed in a 100° C. oil bath for 5 hours. The reaction mixture was concentrated, then diluted with DCM and chloroform. This was washed with water, sat. NaHCO3, and brine, then dried with MgSO4, filtered, and concentrated to give a brown oil. This was purified by HPLC to give 7-(difluoromethoxy)-4-((6-(3-methylisoxazol-5-yl)-[1,2,4]triazolo[4,3-a]pyridin-3-yl)methoxy)quinoline (0.025 g, 13% yield) as the formic acid salt. MS (ESI pos. ion) m/z: 424 (MH+). Calc'd exact mass for C21H15F2N5O3: 423.

Aufarbeitung

  1. customflushed with argon
  2. customsealed
  3. customplaced in a 100° C.
  4. customfor 5 hours
  5. concentrationThe reaction mixture was concentrated
  6. additiondiluted with DCM and chloroform
  7. washThis was washed with water, sat. NaHCO3, and brine
  8. dry with materialdried with MgSO4
  9. filtrationfiltered
  10. concentrationconcentrated
  11. customto give a brown oil
  12. customThis was purified by HPLC

Quellen und Nachweise

ORD-Eintrag
ord-3c483852cdbc403497b1e754dee62bb0
Quelldatensatz
uspto-grants-2013_09
Patentnummer
US08524900B2

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