Ethyl 6-(4-fluorobenzylidene)-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate → ethyl 2-(3-chloro-4-cyanophenyl)-3-(4-fluorophenyl)-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylate

HRID 505715

Reaktionsgleichung

Reaktionsgleichung von HRID 505715
[F:1][C:2]1[CH:24]=[CH:23][C:5]([CH:6]=[C:7]2[CH2:16][CH2:15][C:14]3[CH:13]=[C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])[CH:11]=[CH:10][C:9]=3[C:8]2=O)=[CH:4][CH:3]=1.Cl.[Cl:26][C:27]1[CH:34]=[C:33]([NH:35][NH2:36])[CH:32]=[CH:31][C:28]=1[C:29]#[N:30]>>[Cl:26][C:27]1[CH:34]=[C:33]([N:35]2[CH:6]([C:5]3[CH:23]=[CH:24][C:2]([F:1])=[CH:3][CH:4]=3)[CH:7]3[C:8]([C:9]4[CH:10]=[CH:11][C:12]([C:17]([O:19][CH2:20][CH3:21])=[O:18])=[CH:13][C:14]=4[CH2:15][CH2:16]3)=[N:36]2)[CH:32]=[CH:31][C:28]=1[C:29]#[N:30]

Komponenten

3

Edukt 2

HCID 2740454Ethyl 6-(4-fluorobenzylidene)-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylateHCID 221118492-Chloro-4-hydrazinylbenzonitrile hydrochloride

Produkt 1

HCID 66723029ethyl 2-(3-chloro-4-cyanophenyl)-3-(4-fluorophenyl)-3,3a,4,5-tetrahydro-2H-benzo[g]indazole-7-carboxylateAusbeute 83 %

Versuchsvorschrift

The title compound was prepared from ethyl 6-(4-fluorobenzylidene)-5-oxo-5,6,7,8-tetrahydronaphthalene-2-carboxylate (Preparation 16; 324 mg, 1.0 mmol) and 2-chloro-4-hydrazinylbenzonitrile hydrochloride (Preparation 1; 306 mg, 1.5 mmol) according to Method B (yellow solid, 394 mg, 0.830 mmol, 83% yield). 1H NMR (400 MHz, DMSO-d6) δ ppm 0.80 (m, 1H), 1.31 (t, J=7.12 Hz, 3H), 1.79 (m, 1H), 2.95 (m, 2H), 3.97 (ddd, J=13.49, 11.21, 4.83 Hz, 1H), 4.31 (q, J=6.98 Hz, 2H), 5.94 (d, J=11.28 Hz, 1H), 7.15 (m, 6H), 7.66 (d, J=8.86 Hz, 1H), 7.80 (s, 1H), 7.85 (dd, J=8.19, 1.75 Hz, 1H), 8.16 (d, J=8.06 Hz, 1H). ES-MS m/z 474 (M+H).

Quellen und Nachweise

ORD-Eintrag
ord-724090a91abc48739b49a1b46f127218
Quelldatensatz
uspto-grants-2010_08
Patentnummer
US07781428B2

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