3-Methylsulfonylaminophenylboronic acid → N-[3-(2,8-Dimethoxy-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenyl]-methanesulfonamide

HRID 2218695

Reaktionsgleichung

Reaktionsgleichung von HRID 2218695
[CH3:1][S:2]([NH:5][C:6]1[CH:7]=[C:8](B(O)O)[CH:9]=[CH:10][CH:11]=1)(=[O:4])=[O:3].Br[CH:16]=[C:17]1[C:23]2[CH:24]=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:22]=2[CH2:21][CH2:20][C:19]2[CH:30]=[C:31]([O:34][CH3:35])[CH:32]=[CH:33][C:18]1=2>>[CH3:35][O:34][C:31]1[CH:32]=[CH:33][C:18]2[C:17](=[CH:16][C:8]3[CH:7]=[C:6]([NH:5][S:2]([CH3:1])(=[O:4])=[O:3])[CH:11]=[CH:10][CH:9]=3)[C:23]3[CH:24]=[CH:25][C:26]([O:28][CH3:29])=[CH:27][C:22]=3[CH2:21][CH2:20][C:19]=2[CH:30]=1

Komponenten

3

Edukt 2

HCID 27735353-Methylsulfonylaminophenylboronic acidHCID 689363135-bromomethylene-2,8-dimethoxy-10,11-dihydro-5H-dibenzo[a,d]cycloheptene

Produkt 1

HCID 59770061N-[3-(2,8-Dimethoxy-10,11-dihydro-dibenzo[a,d]cyclohepten-5-ylidenemethyl)-phenyl]-methanesulfonamideAusbeute 39 %

Versuchsvorschrift

Following procedures essentially as described in Example 219, below, and using 3-methanesulfonamidophenyl boronic acid (473 mg, 2.2 mmol) with 5-bromomethylene-2,8-dimethoxy-10,11-dihydro-5H-dibenzo[a,d]cycloheptene (690 mg, 2 mmol) to give 1.3 g crude product. Purify the crude product using column chromatography eluting with 10% EtOAc/hexane to 30% EtOAc/hexane to give 340 mg (39%) product as a pale yellow solid, mp 109.6° C. MS (ES) 436 (M+1), 434 (M−1). HPLC shows 91% purity at t=3.11 min.

Aufarbeitung

  1. customto give 1.3 g crude product
  2. customPurify the crude product
  3. washeluting with 10% EtOAc/hexane to 30% EtOAc/hexane

Quellen und Nachweise

ORD-Eintrag
ord-1c675aa87dda4f2bb07ea253b4c898a0
Quelldatensatz
uspto-grants-2008_08
Patentnummer
US07411072B2

Verknüpfte Notizen

Wird geladen…