Benzophenone imine → 6-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]-N-(diphenylmethylene)pyridin-3-amine

HRID 7792

Reaktionsgleichung

Reaktionsgleichung von HRID 7792
Cl[C:2]1[CH:3]=[CH:4][C:5]([C:8]2[CH:13]=[CH:12][C:11]([C:14]3[O:15][C:16]4[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=4[N:18]=3)=[CH:10][C:9]=2[O:23][CH3:24])=[N:6][CH:7]=1.[C:25](=[NH:38])([C:32]1[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=1)[C:26]1[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=1.C1(C2C=CC=CC=2)C=CC=CC=1P(C1CCCCC1)C1CCCCC1.CC([O-])(C)C.[Na+]>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]>[O:15]1[C:16]2[CH:22]=[CH:21][CH:20]=[CH:19][C:17]=2[N:18]=[C:14]1[C:11]1[CH:12]=[CH:13][C:8]([C:5]2[N:6]=[CH:7][C:2]([N:38]=[C:25]([C:26]3[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=3)[C:32]3[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=3)=[CH:3][CH:4]=2)=[C:9]([O:23][CH3:24])[CH:10]=1

Komponenten

6

Edukt 4

HCID 136809Benzophenone imineHCID 27342162-(Dicyclohexylphosphino)biphenylHCID 103087512-[4-(5-Chloropyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazoleHCID 23676156Sodium t-butoxide

Produkt 1

HCID 219909526-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]-N-(diphenylmethylene)pyridin-3-amine

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysator

Reaktionsbedingungen

Temperatur
80 °C

Versuchsvorschrift

2-[4-(5-chloropyridin-2-yl)-3-methoxyphenyl]-1,3-benzoxazole (100 mg, 0.30 mmol), benzophenone imine (60 μL, 0.36 mmol), Pd2(dba)3 (15 mg, 0.015 mmol), 1,1′-biphenyl-2-yl(dicyclohexyl)phosphine (10 mg, 0.015 mmol), NaOtBu (40 mg, 0.42 mmol) were combined in a sealable tube evacuated and backfilled with argon. Toluene (600 μL) was added and the mixture was degassed with a stream of argon for 5 min. The tube was sealed and the mixture was heated to 80° C. for 24 h. Crude mixture was adsorbed onto silica gel and purified by automated flash chromatography using an EtOAc/hexanes gradient to afford 6-[4-(1,3-benzoxazol-2-yl)-2-methoxyphenyl]-N-(diphenylmethylene)pyridin-3-amine as a yellow solid.

Aufarbeitung

  1. customevacuated
  2. additionToluene (600 μL) was added
  3. customthe mixture was degassed with a stream of argon for 5 min
  4. customThe tube was sealed
  5. custompurified by automated flash chromatography

Quellen und Nachweise

ORD-Eintrag
ord-51f0adc9d41543e1b9f0d008ab664d0d
Quelldatensatz
uspto-grants-2006_08
Patentnummer
US07087601B2

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