Acrylonitrile → 3-iodo-9H-carbazole

HRID 1008659Notes

Reaction equation

C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(N(CC)CC)C.[I:27][C:28]1[CH:29]=[CH:30][C:31]2[NH:32][C:33]3[C:38]([C:39]=2[CH:40]=1)=[CH:37][CH:36]=[CH:35][CH:34]=3.[C:41](#[N:44])[CH:42]=[CH2:43]>C([O-])(=O)C.[Pd+2].C([O-])(=O)C.CCOC(C)=O.CCCCCC.O1CCOCC1>[C:41]([CH:42]=[CH:43][C:28]1[CH:29]=[CH:30][C:31]2[NH:32][C:33]3[C:38]([C:39]=2[CH:40]=1)=[CH:37][CH:36]=[CH:35][CH:34]=3)#[N:44].[I:27][C:28]1[CH:29]=[CH:30][C:31]2[NH:32][C:33]3[C:38]([C:39]=2[CH:40]=1)=[CH:37][CH:36]=[CH:35][CH:34]=3

Participants

Conditions

Temperature: 75 °C

Procedure

To a dioxane solution (10 mL) of triphenylphosphine (139 mg, 0.53 μmol), palladium acetate (40.0 mg, 0.18 μmol) and triethylamine (0.59 μL, 4.23 mmol) were sequentially added, and the mixture was stirred for 5 minutes at 75° C. A dioxane solution (15 mL) of compound 1 (1.03 g, 3.52 mmol) and acrylonitrile (0.46 μL, 7.04 mmol) were added, and the reaction solution was refluxed for 11.5 hours. The product was confirmed by TLC (HexH:AcOEt=4:1), and then the palladium powder was removed by cotton filtration. The product was purified by column chromatography (HexH:AcOEt=4:1), and compound 2 (0.14 g, 18%, trans:cis=97:3) was obtained as a white powder, while compound 1 (0.37 g, recovery rate 37%) was recovered as a white powder.

Workup

temperaturethe reaction solution was refluxed for 11.5 hours
customthe palladium powder was removed by cotton filtration
customThe product was purified by column chromatography (HexH:AcOEt=4:1)

Sources & evidence

ORD record: ord-f5149a68d27c46f0882d718c622b61aa
Source dataset: uspto-grants-2011_07
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07972792B2

Reaction notes

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