Hydrochloric Acid → 4-(2-Chloro-6-methoxyphenyl)-6-(3-hydroxypropyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11050Notes

Reaction equation

HRID 11050 reaction equation
[Si]([O:8][CH2:9][CH2:10][CH2:11][N:12]1[C:24]2[CH2:23][CH:22]([C:25]3[C:30]([O:31][CH3:32])=[CH:29][CH:28]=[CH:27][C:26]=3[Cl:33])[CH:21]3[C:34](=[O:38])[NH:35][C:36](=[O:37])[CH:20]3[C:19]=2[C:18]2[CH:17]=[C:16]([O:39][CH3:40])[CH:15]=[CH:14][C:13]1=2)(C(C)(C)C)(C)C.[Si](OCCCN1C2CC(C3C=CC=CC=3OC)C3C(=O)NC(=O)C3C=2C2C=C(OC)C=CC1=2)(C(C)(C)C)(C)C.C(C1C(=O)C(Cl)=C(Cl)C(=O)C=1C#N)#N.Cl>C1COCC1.CO>[Cl:33][C:26]1[CH:27]=[CH:28][CH:29]=[C:30]([O:31][CH3:32])[C:25]=1[C:22]1[C:21]2[C:34](=[O:38])[NH:35][C:36](=[O:37])[C:20]=2[C:19]2[C:18]3[CH:17]=[C:16]([O:39][CH3:40])[CH:15]=[CH:14][C:13]=3[N:12]([CH2:11][CH2:10][CH2:9][OH:8])[C:24]=2[CH:23]=1

Participants

6

Reactant 4

HCID 313Hydrochloric AcidHCID 67752,3-Dichloro-5,6-dicyano-1,4-benzoquinoneHCID 697144596-(3-{[tert-Butyl(dimethyl)silyl]oxy}propyl)-4-(2-chloro-6-methoxyphenyl)-9-methoxy-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2H,3aH)-dioneHCID 867601946-(3-{[Tert-butyl(dimethyl)silyl]oxy}propyl)-9-methoxy-4-(2-methoxyphenyl)-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2h, 3ah)-dione

Product 1

HCID 867601964-(2-Chloro-6-methoxyphenyl)-6-(3-hydroxypropyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 76%

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The reaction of 6-(3-{[tert-Butyl(dimethyl)silyl]oxy}propyl)-4-(2-chloro-6-methoxyphenyl)-9-methoxy-4,5,6,10c-tetrahydropyrrolo[3,4-c]carbazole-1,3(2H,3aH)-dione (IV; Ar=2-chloro-6-methoxyphenyl, R10═CH2CH2CH2OSiMe2t-Bu) (104) prepared as described in example 57 with DDQ using the procedure described in example 70 followed by reaction with 2N HCl in THF/methanol gave 4-(2-Chloro-6-methoxyphenyl)-6-(3-hydroxypropyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione (V; Ar=2-chloro-6-methoxyphenyl, R10═CH2CH2CH2OH) (105) in a 76% yield as an orange powder; mp 224–227° C. 1H NMR δ [(CD3)2SO] 11.05 (br, 1H), 8.51 (d, J=2.6 Hz, 1H), 7.75 (s, 1H), 7.69 (d, J=8.9 Hz, 1H), 7.44 (dd, J=8.2, 8.2 Hz, 1H), 7.31 (dd, J=8.9, 2.6 Hz, 1H), 7.18 (d, J=8.2 Hz, 1H), 7.13 (d, J=8.2 Hz, 1H), 4.63 (t, J=4.9 Hz, 1H), 4.51 (t, J=6.8 Hz, 2H), 3.91 (s, 3H), 3.68 (s, 3H), 3.41 (m, 2H), 1.89 (m, 2H). Found: C, 69.71; H, 4.53; N, 6.43. C25H22N2O5 requires C, 69.76; H, 5.15; N, 6.51.

Sources & evidence

ORD record
ord-8af552d326f44e5488dc65134040e607
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Reaction notes

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