6-(1-(3-nitrophenyl)-vinyl)-3-styryl-1-[2-(trimethyl-silanyl)-ethoxymethyl]1H-indazole → 6-(1-(3-Aminophenyl)-vinyl)-3-styryl-1H-indazole

HRID 1816810Notes

Reaction equation

HRID 1816810 reaction equation
[N+:1]([C:4]1[CH:5]=[C:6]([C:10]([C:12]2[CH:20]=[C:19]3[C:15]([C:16]([CH:29]=[CH:30][C:31]4[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=4)=[N:17][N:18]3COCC[Si](C)(C)C)=[CH:14][CH:13]=2)=[CH2:11])[CH:7]=[CH:8][CH:9]=1)([O-])=O.NC1C=C(C(C2C=C3C(C(C=CC4C=CC=CC=4)=NN3COCC[Si](C)(C)C)=CC=2)=C)C=CC=1>C(OCC)(=O)C.CCCCCC>[NH2:1][C:4]1[CH:5]=[C:6]([C:10]([C:12]2[CH:20]=[C:19]3[C:15]([C:16]([CH:29]=[CH:30][C:31]4[CH:32]=[CH:33][CH:34]=[CH:35][CH:36]=4)=[N:17][NH:18]3)=[CH:14][CH:13]=2)=[CH2:11])[CH:7]=[CH:8][CH:9]=1

Participants

4

Reactant 2

HCID 693714336-(1-(3-nitrophenyl)-vinyl)-3-styryl-1-[2-(trimethyl-silanyl)-ethoxymethyl]1H-indazoleHCID 693721006-(1-(3-Aminophenyl)-vinyl)-3-styryl 1-[2-trimethylsilanyl-ethoxymethyl]-1H-indazole

Product 1

HCID 693711396-(1-(3-Aminophenyl)-vinyl)-3-styryl-1H-indazole

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

6-(1-(3-Nitrophenyl)-vinyl)-3-styryl-1-[2-(trimethyl-silanyl)-ethoxymethyl]-1H-indazole was converted to 6-(1-(3-aminophenyl)-vinyl)-3-styryl-1-[2-(trimethyl-silanyl)-ethoxymethyl]-1H-indazole as described in Example 11, step (iv) (140 mg, 95%): Rf sm 0.59, p 0.46 (ethyl acetate-hexane 4:6); FTIR (thin film) 3460, 3366, 3223, 3084, 3028, 2952, 2894, 2246, 1616, 1601, 1581, 1489, 1474, 1448, 1359.1303, 1249, 1217, 1076, 961, 909, 860, 836, 733, 692 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.96 (d, 1H, J=8.5 Hz), 7.59 (m, 3H), 7.50 (s, 1H), 7.46 (s, 1H), 7.40 (m, 2H), 7.30 (m, 1H), 7.25 (m, 1H), 7.14 (m, 1H), 6.77 (m, 1H), 6.68 (m, 2H); 13C NMR (75 MHz, CDCl3) δ 151.6, 147.7, 144.6, 143.9, 142.8, 142.4, 138.6, 132.8, 130.6, 130.2, 129.3, 128.0, 124.4, 123.6, 121.9, 121.5, 120.2, 116.4, 116.1, 110.8, 79.0, 67.9, 19.2, 0.0; HRMS (FAB) [M+Na]/z Calc'd 490.2291, found 490.2302.

Sources & evidence

ORD record
ord-c4138aea62ba4223b359c00dd66c2bb5
Source dataset
uspto-grants-2005_04
Patent number
US06884890B2

Reaction notes

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