1,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine) → HCID 89761791, Verbindung

HRID 528622Notizen

Reaktionsgleichung

Reaktionsgleichung von HRID 528622
Br[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[O:8][CH2:9][CH2:10][O:11][CH3:12].[CH3:13][O:14][C:15]1[CH:40]=[CH:39][C:18]([CH2:19][N:20]([C:34]2[S:35][CH:36]=[CH:37][N:38]=2)[S:21]([C:24]2[CH:25]=[CH:26][C:27]3[NH:32][CH2:31][CH2:30][O:29][C:28]=3[CH:33]=2)(=[O:23])=[O:22])=[CH:17][CH:16]=1.CC1(C)C2C(=C(P(C3C=CC=CC=3)C3C=CC=CC=3)C=CC=2)OC2C(P(C3C=CC=CC=3)C3C=CC=CC=3)=CC=CC1=2.CC(C)([O-])C.[Na+]>C1(C)C=CC=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.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].[Pd]>[CH3:13][O:14][C:15]1[CH:16]=[CH:17][C:18]([CH2:19][N:20]([C:34]2[S:35][CH:36]=[CH:37][N:38]=2)[S:21]([C:24]2[CH:25]=[CH:26][C:27]3[N:32]([C:2]4[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=4[O:8][CH2:9][CH2:10][O:11][CH3:12])[CH2:31][CH2:30][O:29][C:28]=3[CH:33]=2)(=[O:23])=[O:22])=[CH:39][CH:40]=1

Komponenten

7

Edukt 4

HCID 6360441,1'-(9,9-Dimethyl-9H-xanthene-4,5-diyl)bis(1,1-diphenylphosphine)HCID 137209681-Bromo-2-(2-methoxyethoxy)benzeneHCID 23676156Sodium t-butoxideHCID 89761436N-(4-methoxybenzyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide

Produkt 1

HCID 89761791HCID 89761791, VerbindungAusbeute 44,4 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 9811564Bis(dibenzylideneacetone)palladiumKatalysatorHCID 1140TolueneLösungsmittel

Reaktionsbedingungen

Temperatur
100 °C

Versuchsvorschrift

A mixture of 1-bromo-2-(2-methoxyethoxyl)benzene (302.0 mg, 1.31 mmol), INTERMEDIate M (500 mg, 1.19 mmol), Pd2(dba)3 (76.0 mg, 0.0837 mmol), Xantphos (69.0 mg, 0.119 mmol) and sodium-tert-butoxide (229.0 mg, 2.39 mmol) in toluene (10 mL) was degassed with nitrogen for 10 minutes. The reaction mixture was subjected for heating at 100° C. for 1 h under microwave. After completion, the reaction mixture was diluted with water (10 mL) and extracted with ethyl acetate (3×15 mL). The organic layer was dried over sodium sulfate and concentrated under reduced pressure to obtain the crude material which was purified by combiflash column chromatography (column size: 12 g; elution: 12% ethyl acetate in hexane) to get N-(4-methoxybenzyl)-4-(2-(2-methoxyethoxyl)phenyl)-N-(thiazol-2-yl)-3,4-dihydro-2H-benzo[b][1,4]oxazine-7-sulfonamide (300 mg, 44.2%) as yellow solid. MS (ESI, positive ion) m/z: 568.03 (M+1).

Aufarbeitung

  1. customwas degassed with nitrogen for 10 minutes
  2. additionAfter completion, the reaction mixture was diluted with water (10 mL)
  3. extractionextracted with ethyl acetate (3×15 mL)
  4. dry with materialThe organic layer was dried over sodium sulfate
  5. concentrationconcentrated under reduced pressure
  6. customto obtain the crude material which
  7. customwas purified by combiflash column chromatography (column size: 12 g; elution: 12% ethyl acetate in hexane)

Quellen und Nachweise

ORD-Eintrag
ord-651770def0d14f7a9e004fab761c2430
Quelldatensatz
uspto-grants-2016_05
Patentnummer
US09346798B2

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