4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-6-(2-hydroxyethyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione → 9-Hydroxy-6-(2-hydroxyethyl)-4-(2-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione
Reaction equation
Cl[C:2]1[CH:7]=[CH:6][CH:5]=[C:4]([O:8][CH3:9])[C:3]=1[C:10]1[C:22]2[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:21]=2[C:20]2[C:19]3[CH:18]=[C:17]([OH:28])[CH:16]=[CH:15][C:14]=3[N:13]([CH2:29][CH2:30][OH:31])[C:12]=2[CH:11]=1.[H][H]>[Pd]>[OH:28][C:17]1[CH:16]=[CH:15][C:14]2[N:13]([CH2:29][CH2:30][OH:31])[C:12]3[CH:11]=[C:10]([C:3]4[CH:2]=[CH:7][CH:6]=[CH:5][C:4]=4[O:8][CH3:9])[C:22]4[C:23](=[O:27])[NH:24][C:25](=[O:26])[C:21]=4[C:20]=3[C:19]=2[CH:18]=1Participants
Reactant 2
Product 1
Reagents, catalysts & solvents 1
Procedure
Reaction of 4-(2-Chloro-6-methoxyphenyl)-9-hydroxy-6-(2-hydroxyethyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (VI; Ar-2-chloro-6-methoxyphenyl, R10═CH2CH,OH) (112) prepared as described in example 64 with hydrogen gas, using a Pd/C catalyst, according to the procedure for example 60 gave 9-Hydroxy-6-(2-hydroxyethyl)-4-(2-methoxyphenyl)pyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (VI; Ar=2-methoxyphenyl, R10═CH2CH2OH) (113) in a 77% yield as a yellow solid; mp 285–289° C. 1H NMR δ [(CD3)2SO] 10.91 (br s, 1H), 9.29 (br s, 1H), 8.37 (d, J=2.4 Hz, 1H), 7.70 (s, 1H), 7.55 (d, J=8.8 Hz, 1H), 7.42 (m, 1H), 7.33 (dd, J=8.8, 2.4 Hz, 1H), 7.12–7.02 (m, 3H), 4.84 (t, J=5.5 Hz, 1H), 4.73 (t, J=5.3 Hz, 2H), 3.76 (dt, J=5.5, 5.3 Hz, 2H), 3.68 (s, 3H). Found: C, 67.30; H, 4.47; N, 6.79. C23H18N2O5.1/2H2O requires C, 67.15; H, 4.65; N, 6.81.
Sources & evidence
- ORD record
- ord-4f79f664c86445d28a8aee5c0bd56414
- Source dataset
- uspto-grants-2006_08
- Patent number
- US07094798B1
Reaction notes
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