Dimethylformamide → 3,7-Bis-(4-bromo-phenyl)-1,5-dioctyl-1H,5H-pyrrolo[2,3-f]indole-2,6-dione

HRID 926660Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2C(=O)NC3[C:19]=2[CH:18]=[C:17]2[C:13](=[C:14]([C:21]4[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=4)[C:15](=[O:20])[NH:16]2)[CH:12]=3)=[CH:4][CH:3]=1.[CH3:29][N:30]([CH3:33])[CH:31]=[O:32].C(=O)([O-])[O-].[K+].[K+].Br[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]>CO>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:31](=[O:32])[N:30]([CH2:33][CH2:6][CH2:7][CH2:2][CH2:3][CH2:4][CH2:5][CH3:8])[C:29]3[C:19]=2[CH:18]=[C:17]2[C:13](=[C:14]([C:21]4[CH:26]=[CH:25][C:24]([Br:27])=[CH:23][CH:22]=4)[C:15](=[O:20])[N:16]2[CH2:41][CH2:42][CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[CH:12]=3)=[CH:4][CH:3]=1

Participants

Conditions

Temperature: 90 °C

Procedure

3,7-Bis-(4-bromo-phenyl)-1H,5H-pyrrolo[2,3-f]indole-2,6-dione (1.250 g, 2.519 mmol) (1.3) is dissolved into anhydrous dimethylformamide (50 cm3) and then potassium carbonate (3.482 g, 25.19 mmol) and 1-bromo-octane (1.1 cm3, 6.3 mmol) is added. The resulting mixture is heated to 90° C. for 21 hours before being cooled down, poured into methanol (500 cm3) and filtered to recover the pure product (1.320 g, Yield: 73%). NMR (1H, 300 MHz, CDCl3): δ 7.64 (d, J=8.7 Hz, 4H); 7.57 (d, J=8.7 Hz, 4H); 6.26 (s, 2H); 3.62 (t, J=7.1 Hz, 4H); 1.63 (m, 4H); 1.32 (m, 8H); 1.26 (m, 12H); 0.87 (t, J=6.8 Hz, 6H).

Workup

temperaturebefore being cooled down
filtrationfiltered

Sources & evidence

ORD record: ord-a89edf85823941f7a3b905c92d48ef2d
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09287504B2

Reaction notes

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