Methanol → N2-(2-chlorophenyl)-N2-(2-hydroxyethyl)-N8-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,8-dicarboxamide

HRID 84458

Reaktionsgleichung

Reaktionsgleichung von HRID 84458
Br[C:2]1[CH:3]=[CH:4][C:5]2[C:11]3[S:12][C:13]([C:15]([N:17]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[Cl:27])[CH2:18][CH2:19][OH:20])=[O:16])=[CH:14][C:10]=3[CH2:9][CH2:8][O:7][C:6]=2[CH:28]=1.C[OH:30].CN.C1CCN2[C:36](=[N:37][CH2:38]CC2)CC1>C1COCC1.C(OCC)(=O)C.[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[C-]#[O+].[Mo]>[Cl:27][C:22]1[CH:23]=[CH:24][CH:25]=[CH:26][C:21]=1[N:17]([CH2:18][CH2:19][OH:20])[C:15]([C:13]1[S:12][C:11]2[C:5]3[CH:4]=[CH:3][C:2]([C:38]([NH:37][CH3:36])=[O:30])=[CH:28][C:6]=3[O:7][CH2:8][CH2:9][C:10]=2[CH:14]=1)=[O:16]

Komponenten

8

Edukt 4

HCID 887MethanolHCID 6329MethylamineHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 579003718-bromo-N-(2-chlorophenyl)-N-(2-hydroxyethyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide

Produkt 1

HCID 44242492N2-(2-chlorophenyl)-N2-(2-hydroxyethyl)-N8-methyl-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2,8-dicarboxamideAusbeute 4,3 %

Reagenzien, Katalysatoren, Lösungsmittel 3

HCID 98885Molybdenum carbonyl (Mo(CO)6)KatalysatorHCID 8028TetrahydrofuranLösungsmittel2×HCID 8857Ethyl AcetateLösungsmittel

Versuchsvorschrift

Under ambient conditions a sealable reaction vessel was charged with 8-bromo-N-(2-chlorophenyl)-N-(2-hydroxyethyl)-4,5-dihydrobenzo[b]thieno[2,3-d]oxepine-2-carboxamide (0.08 g, 0.17 mmol), molybdenum hexacarbonyl (0.044 g, 0.167 mmol) in methanol (0.5 ml, 10 mmol)/THF 1 ml, 10 mmol), followed by the addition of 2M methylamine in THF (0.251 ml),/trans-D(mu-acetato)bis[di-o-tolylphosphino)benzyl]dipalladium(II) (32.3 mg, 0.0334 mmol). Finally, DBU (0.025 ml, 0.167 mmol) was added and the reaction vial was quickly sealed. The charged reaction vial was flash heated on a Biotage Emrys Optimizer microwave at 150° C. for 20 minutes. The cooled reaction mixture was diluted with ethyl acetate and filtered through a bed of Celite. The filtrate was concentrated to a solid and purified by MPLC on silica to give 3.2 mg 154 (yield=4.3% of theoretical). MS: (ESI+) 458.2

Aufarbeitung

  1. customthe reaction vial was quickly sealed
  2. customThe charged reaction
  3. temperatureheated on a Biotage
  4. customThe cooled reaction mixture
  5. filtrationfiltered through a bed of Celite
  6. concentrationThe filtrate was concentrated to a solid
  7. custompurified by MPLC on silica

Quellen und Nachweise

ORD-Eintrag
ord-48a9550556d446a4afc009804e7a23c9
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08846762B2

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