Allyltributylstannane → 4-Allyl-2-chloro-N-(1-hydroxy-3,3-dimethyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-benzamide

HRID 60559

Reaktionsgleichung

Reaktionsgleichung von HRID 60559
[Cl:1][C:2]1[CH:22]=[C:21]([CH:23]=[CH2:24])[CH:20]=[CH:19][C:3]=1[C:4]([NH:6][C:7]1[CH:8]=[CH:9][C:10]2[C:14]([CH3:16])([CH3:15])[O:13][B:12]([OH:17])[C:11]=2[CH:18]=1)=[O:5].[CH2:25]([Sn](CCCC)(CCCC)CCCC)C=C>>[CH2:23]([C:21]1[CH:20]=[CH:19][C:3]([C:4]([NH:6][C:7]2[CH:8]=[CH:9][C:10]3[C:14]([CH3:16])([CH3:15])[O:13][B:12]([OH:17])[C:11]=3[CH:18]=2)=[O:5])=[C:2]([Cl:1])[CH:22]=1)[CH:24]=[CH2:25]

Komponenten

3

Edukt 2

HCID 90628AllyltributylstannaneHCID 669274352-Chloro-N-(1-hydroxy-3,3-dimethyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-4-vinyl-benzamide

Produkt 1

HCID 673582964-Allyl-2-chloro-N-(1-hydroxy-3,3-dimethyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-benzamide

Versuchsvorschrift

The title compound was prepared using a procedure similar to that of 2-chloro-N-(1-hydroxy-3,3-dimethyl-1,3-dihydro-benzo[c][1,2]oxaborol-6-yl)-4-vinyl-benzamide with allyltributyltin replacing tributyl(vinyl)tin. Data: LCMS (M/Z): 356 (M+H); 1H NMR (DMSO-d6) δ: 1.44 (s, 6 H) 3.44 (d, J=6.8 Hz, 2 H) 5.04-5.22 (m, 2 H) 5.87-6.06 (m, 1 H) 7.28 (d, J=9.0 Hz, 1 H) 7.35-7.41 (m, 2 H) 7.50 (s, 1 H) 7.68 (dd, J=8.3, 2.0 Hz, 1 H) 8.05 (d, J=1.8 Hz, 1 H) 9.09 (br. s., 1 H) 10.45 (s, 1 H).

Quellen und Nachweise

ORD-Eintrag
ord-2e8b68360de6468b9c3ad28b9403ada2
Quelldatensatz
uspto-grants-2016_09
Patentnummer
US09440994B2

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