Sodium Carbonate → N-({6-[(E)-2-cyclohexylvinyl]pyridin-2-yl}methoxy)-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

HRID 1258566Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 1258566
Br[C:2]1[N:7]=[C:6]([CH2:8][O:9][N:10]=[C:11]([C:18]2[N:22]([CH3:23])[N:21]=[N:20][N:19]=2)[C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[CH:5]=[CH:4][CH:3]=1.[CH:24]1(/[CH:30]=[CH:31]/B(O)O)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1.C([O-])([O-])=O.[Na+].[Na+]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1.C1(C)C=CC=CC=1.C(O)C.O>[CH:24]1(/[CH:30]=[CH:31]/[C:2]2[N:7]=[C:6]([CH2:8][O:9][N:10]=[C:11]([C:18]3[N:22]([CH3:23])[N:21]=[N:20][N:19]=3)[C:12]3[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=3)[CH:5]=[CH:4][CH:3]=2)[CH2:29][CH2:28][CH2:27][CH2:26][CH2:25]1

Komponenten

6

Edukt 3

HCID 10340Sodium CarbonateHCID 6031024(2-Cyclohexylvinyl)boronic acidHCID 86653112N-[(6-bromopyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine

Produkt 1

HCID 86653122N-({6-[(E)-2-cyclohexylvinyl]pyridin-2-yl}methoxy)-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimineAusbeute 71,8 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 178418397HCID 178418397, VerbindungKatalysatorHCID 86587398Ethanol toluene waterLösungsmittel

Reaktionsbedingungen

Temperatur
90 °C

Versuchsvorschrift

In a dried and purged vessel were added N-[(6-bromopyridin-2-yl)methoxy]-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.2 g, 0.536 mmol, 1 eq.), [(E)-2-cyclohexylvinyl]boronic acid (0.090 g, 0.58 mmol, 1.1 eq.), Na2CO3 (0.119 g, 1.12 mmol, 2.1 eq.) and Tetrakis(triphenylphosphine)palladium (0.030 g, 0.027 mmol, 0.05 eq.). A mixture of solvent was added toluene/ethanol/water (4/1/1) was added and the vessel purged with argon and sealed. The reaction was heated to 90° C. for 6 hrs. After cooling, 10 ml of EtOAc were added and the solids were filtered through a “Celite” plug and washed with EtOAc. The organics were separated, dried over MgSO4 and concentrated. The residue was purified by chromatography on silica gel to give N-({6-[(E)-2-cyclohexylvinyl]pyridin-2-yl}methoxy)-1-(1-methyl-1H-tetrazol-5-yl)-1-phenylmethanimine (0.155 g, 68% yield) as a colorless gum.

Aufarbeitung

  1. customIn a dried
  2. custompurged vessel
  3. additionA mixture of solvent
  4. additionwas added
  5. customthe vessel purged with argon
  6. customsealed
  7. temperatureAfter cooling
  8. addition10 ml of EtOAc were added
  9. filtrationthe solids were filtered through a “Celite” plug
  10. washwashed with EtOAc
  11. customThe organics were separated
  12. dry with materialdried over MgSO4
  13. concentrationconcentrated
  14. customThe residue was purified by chromatography on silica gel

Quellen und Nachweise

ORD-Eintrag
ord-8a6baf1f9ba24c2ca5bb57275d695bc5
Quelldatensatz
uspto-grants-2013_06
Patentnummer
US08466176B2

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