M-Phenylenediamine → N-methyl-N-(3-styryl-1H-indazol-6-yl)-benzene-1,3-diamine

HRID 2181517Notes

Reaction equation

HRID 2181517 reaction equation
[CH3:1][N:2]([C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([N+:34]([O-])=O)[CH:29]=1)[C:3]1[CH:11]=[CH:10][CH:9]=[C:8]2[C:4]=1[C:5]([CH:20]=[CH:21][C:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1)=[N:6][N:7]2COCC[Si](C)(C)C.C1(N)C=CC=C(N)C=1>C(OCC)(=O)C.CCCCCC>[CH3:1][N:2]([C:3]1[CH:4]=[C:8]2[C:9]([C:5]([CH:20]=[CH:21][C:22]3[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=3)=[N:6][NH:7]2)=[CH:10][CH:11]=1)[C:28]1[CH:33]=[CH:32][CH:31]=[C:30]([NH2:34])[CH:29]=1

Participants

4

Reactant 2

HCID 7935M-PhenylenediamineHCID 69731757HCID 69731757, compound

Product 1

HCID 69370903N-methyl-N-(3-styryl-1H-indazol-6-yl)-benzene-1,3-diamine

Reagents, catalysts & solvents 1

HCID 21226206Ethyl acetate hexaneSolvent

Procedure

Methyl-(3-nitro-phenyl)-{3-styryl-1-[2-(trimethyl-silanyl)-ethoxymethyl)-1H-indazol-yl}-amine was converted to N-methyl-N{3-styryl-1-[2-trimethyl-silanyl)-ethoxymethyl]-1H-indazol-6-yl}-benzene-1,3-diamine as described in Example 11, step (iv). Rf sm 0.55, Rf p 0.31 (ethyl acetate:hexane 3:7); FTIR (thin film) 3455, 3360, 2951, 2893, 1621, 1601, 1494, 1449, 1249, 1074 cm−1; 1H NMR (300 MHz, CDCl3) δ 7.81 (d, 1H, J=8.8 Hz) 7.58 (d, 2H, J=7.21 Hz), 7.26-7.50 (m, 5H), 7.12 (t, 1H, J=7.93 Hz), 7.01 (d, 1H, J=1.73 Hz), 6.95 (dd, 1H, J=1.99, 8.85 Hz), 5.67 (s, 2H), 3.63 (t, 2H, J=8.12 Hz), 3.38 (s, 3H), 0.93 (t, 2H, J=8.13 Hz), −0.04 (s, 9H); 13C NMR (75 MHz, CDCl3) δ 150.3, 149.0, 147.7, 143.4, 143.0, 137.6, 131.3, 130.4, 128.9, 128.0, 126.7, 121.2, 120.6, 117.3, 117.0, 113.1, 110.1, 109.3, 97.5, 77.8, 66.6, 41.0, 18.0, −1.2; LCMS (ESI) [M+H]/z Calc'd 471, Found 471.

Sources & evidence

ORD record
ord-ca3542f3e52e4ddaa0492966fddb3c29
Source dataset
uspto-grants-2005_05
Patent number
US06891044B2

Reaction notes

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