Sodium Carbonate → Methyl 3-amino-7-chlorobenzo[b]thiophene-2-carboxylate

HRID 235064

Reaktionsgleichung

Reaktionsgleichung von HRID 235064
Cl[C:2]1[C:9]([Cl:10])=[CH:8][CH:7]=[CH:6][C:3]=1[C:4]#[N:5].[C:11]([O:15][CH3:16])(=[O:14])[CH2:12][SH:13].C(=O)([O-])[O-].[Na+].[Na+].CCCCCC.CCOC(C)=O>CO>[NH2:5][C:4]1[C:3]2[CH:6]=[CH:7][CH:8]=[C:9]([Cl:10])[C:2]=2[S:13][C:12]=1[C:11]([O:15][CH3:16])=[O:14]

Komponenten

6

Edukt 4

HCID 10340Sodium CarbonateHCID 16907Methyl ThioglycolateHCID 7365672,3-DichlorobenzonitrileHCID 21226206Ethyl acetate hexane

Produkt 1

HCID 10633878Methyl 3-amino-7-chlorobenzo[b]thiophene-2-carboxylateAusbeute 12 %

Reagenzien, Katalysatoren, Lösungsmittel 1

HCID 887MethanolLösungsmittel

Versuchsvorschrift

The product from Example 56B (1.7 g, 10 mmol) was treated with 1 eq of methyl thioglycolate and 1 eq sodium carbonate in methanol as described in Example 41A to give after chromatography (4:1 hexane/EtOAc) the title compound in 12% yield. 1H NMR (300 MHz, CDCl3) d 3.81 (s, 3H), 5.90 (bs, 2H), 7.34 (t, J=8 Hz, 1H), 7.48 (dd, J=8.1 Hz, 1H), 7.56 (dd, J=8,1 Hz, 1H). MS (DCI/NH3) m/e 259 (M+NH4)+.

Quellen und Nachweise

ORD-Eintrag
ord-2d1f40fbfd304d09b30758f3d71fe289
Quelldatensatz
uspto-grants-1997_01
Patentnummer
US05597823

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