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

HRID 926661Notes

Reaction equation

[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[C:9](=O)[NH:10][C:11]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])[NH:16]2)[CH:12]=3)=[CH:4][CH:3]=1.CN(C)C=O.[C:34](=[O:37])([O-])[O-].[K+].[K+].Br[CH2:41][CH:42]([CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48]>CO>[Br:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:34](=[O:37])[N:10]([CH2:9][CH:8]([CH2:5][CH2:4][CH2:3][CH2:2][CH2:7][CH3:6])[CH2:19][CH2:18][CH2:17][CH2:13][CH2:14][CH2:21][CH2:22][CH3:23])[C:11]3[C:19]=2[CH:18]=[C:17]2[C:13](=[C:14]([C:21]4[CH:22]=[CH:23][C:24]([Br:27])=[CH:25][CH:26]=4)[C:15](=[O:20])[N:16]2[CH2:41][CH:42]([CH2:43][CH2:44][CH2:45][CH2:46][CH2:47][CH3:48])[CH2:49][CH2:50][CH2:51][CH2:52][CH2:53][CH2:54][CH2:55][CH3:56])[CH:12]=3)=[CH:6][CH:7]=1

Participants

Conditions

Temperature: 90 °C

Procedure

3,7-Bis-(4-bromo-phenyl)-1H,5H-pyrrolo[2,3-f]indole-2,6-dione (1.500 g, 3.023 mmol) (1.3) is dissolved into anhydrous dimethylformamide (60 cm3) and then potassium carbonate (4.178 g, 30.23 mmol) and 7-bromomethyl-pentadecane (2.308 g, 7.558 mmol) are added. The resulting mixture is heated to 90° C. for 21 hours before been cooling down, poured into methanol (400 cm3), filtered and washed with water (200 cm3) to recover the pure product (1.525 g, Yield: 53%). NMR (1H, 300 MHz, CDCl3): δ 7.61 (d, J=8.7 Hz, 4H), 7.57 (d, J=8.6 Hz, 4H), 6.29 (s, 2H), 3.50 (d, J=7.3 Hz, 4H), 1.76 (m, 2H), 1.28 (m, 48H), 0.86 (t, J=7.1 Hz, 12H)

Workup

temperaturebefore been cooling down
filtrationfiltered
washwashed with water (200 cm3)

Sources & evidence

ORD record: ord-c71613391358401499eb890a861e7fba
Source dataset: uspto-grants-2016_03
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09287504B2

Reaction notes

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