Homoallyl bromide → 6-(3-Butenyl)-4-(2-chlorophenyl)-2-(2,4-dimethoxybenzyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

HRID 11130

Reaction equation

HRID 11130 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[C:8]1[C:20]2[C:21](=[O:36])[N:22]([CH2:25][C:26]3[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=3[O:34][CH3:35])[C:23](=[O:24])[C:19]=2[C:18]2[C:17]3[CH:16]=[C:15]([O:37][CH3:38])[CH:14]=[CH:13][C:12]=3[NH:11][C:10]=2[CH:9]=1.Br[CH2:40][CH2:41][CH:42]=[CH2:43]>>[CH2:43]([N:11]1[C:10]2[CH:9]=[C:8]([C:3]3[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=3[Cl:1])[C:20]3[C:21](=[O:36])[N:22]([CH2:25][C:26]4[CH:31]=[CH:30][C:29]([O:32][CH3:33])=[CH:28][C:27]=4[O:34][CH3:35])[C:23](=[O:24])[C:19]=3[C:18]=2[C:17]2[CH:16]=[C:15]([O:37][CH3:38])[CH:14]=[CH:13][C:12]1=2)[CH2:42][CH:41]=[CH2:40]

Participants

3

Reactant 2

HCID 21241Homoallyl bromideHCID 118430084-(2-Chlorophenyl)-2-(2,4-dimethoxybenzyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dione

Product 1

HCID 219804596-(3-Butenyl)-4-(2-chlorophenyl)-2-(2,4-dimethoxybenzyl)-9-methoxypyrrolo[3,4-c]carbazole-1,3(2H,6H)-dioneYield 58.4%

Procedure

Reaction of carbazole (287) (260 mg, 0.51 mmol) prepared as described in example 297 with 4-bromo-1-butene (155 □L, 1.53 mmol) according to procedure described in example 298 gave carbazole (289) (173 mg, 58%) as a yellow powder, mp 161–164° C. 1H NMR δ [(CD3)2SO] 8.50 (d, J=2.6 Hz, 1H), 7.89 (s, 1H), 7.73 (d, J=9.0 Hz, 1H), 7.60–7.46 (m, 4H), 7.31 (dd, J=9.0, 2.6 Hz, 1H), 6.96 (d, J=8.5 Hz, 1H), 6.57 (d, J=2.3 Hz, 1H), 6.44 (dd, J=8.4, 2.3 Hz, 1H), 5.84 (m, 1H), 4.96–4.86 (m, 2H), 4.68 (s, 2H), 4.60 (t, J=6.9 Hz, 2H), 3.89 (s, 3H), 3.80 (s, 3H), 3.72 (s, 3H), 2.54 (partially obscured m, 2H). Found: C, 70.23; H, 5.15; N, 4.91. C34H29ClN2O5 requires: C, 70.28; H, 5.03; N, 4.82.

Workup

  1. customprepared

Sources & evidence

ORD record
ord-600ccf5b9b9540ba9a97d77d8ba42995
Source dataset
uspto-grants-2006_08
Patent number
US07094798B1

Linked notes

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