Phenylsilane → 5-Phenyl-3-(tetrahydro-thiopyran-4-ylamino)-thiophene-2-carboxylic acid methyl ester

HRID 73205

Reaktionsgleichung

Reaktionsgleichung von HRID 73205
[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH2:10])=[O:4].[S:17]1[CH2:22][CH2:21][C:20](=O)[CH2:19][CH2:18]1.C1([SiH3])C=CC=CC=1>C1COCC1.[Sn](CCCC)(CCCC)(Cl)Cl>[CH3:1][O:2][C:3]([C:5]1[S:6][C:7]([C:11]2[CH:16]=[CH:15][CH:14]=[CH:13][CH:12]=2)=[CH:8][C:9]=1[NH:10][CH:20]1[CH2:21][CH2:22][S:17][CH2:18][CH2:19]1)=[O:4]

Komponenten

6

Edukt 3

HCID 12752PhenylsilaneHCID 66173Tetrahydrothiopyran-4-oneHCID 700562Methyl 3-amino-5-phenylthiophene-2-carboxylate

Produkt 1

HCID 597523745-Phenyl-3-(tetrahydro-thiopyran-4-ylamino)-thiophene-2-carboxylic acid methyl esterAusbeute 56,5 %

Reagenzien, Katalysatoren, Lösungsmittel 2

HCID 12688Dibutyltin dichlorideKatalysatorHCID 8028TetrahydrofuranLösungsmittel

Versuchsvorschrift

Reductive amination of 3-amino-5-phenyl-thiophene-2-carboxylic acid methyl ester (0.933 g, 4.0 mmol) and tetrahydro-thiopyran-4-one (0.464 g, 4.0 mmol) in THF (1.0 mL) employing Bu2SnCl2 (60.5 mg, 0.2 mmol) and PhSiH3 (0.476 g, 0.542 mL) was carried out as described for example 13, step 1 gave 5-phenyl-3-(tetrahydro-thiopyran-4-ylamino)-thiophene-2-carboxylic acid methyl ester (0.753 g, 56.3%). NMR 1H (CDCl3, 400 MHz): 7.64-7.6 (m, 2H), 7.44-7.34 (m, 3H), 6.9 (brm, 1H), 6.81 (brs, 1H), 3.84 (s, 3H), 3.5-3.4 (m, 1H), 2.85-2.7 (m, 4H), 2.4-2.25 (m, 2H), 1.85-1.7 (m, 2H).

Quellen und Nachweise

ORD-Eintrag
ord-9887b9a5d4de4344accb803ab0a9f125
Quelldatensatz
uspto-grants-2014_09
Patentnummer
US08829030B2

Verknüpfte Notizen

Wird geladen…