Water → 2,6-di(9H-carbazol-9-yl)pyridine

HRID 1037507Notes

Reaction equation

[CH:1]1[C:13]2[NH:12][C:11]3[C:6](=[CH:7][CH:8]=[CH:9][CH:10]=3)[C:5]=2[CH:4]=[CH:3][CH:2]=1.Cl[C:15]1[CH:20]=[CH:19][CH:18]=[C:17](Cl)[N:16]=1.[H-].[Na+].O>CN(C=O)C>[CH:10]1[C:11]2[N:12]([C:15]3[CH:20]=[CH:19][CH:18]=[C:17]([N:12]4[C:13]5[CH:1]=[CH:2][CH:3]=[CH:4][C:5]=5[C:6]5[C:11]4=[CH:10][CH:9]=[CH:8][CH:7]=5)[N:16]=3)[C:13]3[C:5](=[CH:4][CH:3]=[CH:2][CH:1]=3)[C:6]=2[CH:7]=[CH:8][CH:9]=1

Participants

Conditions

Temperature: 160 °C

Procedure

To a solution of carbazole (97.0 g, 0.58 mol) and 2,6-dichloropyridine (41.0 g, 0.28 mol) in dry DMF (200.0 ml) was slowly added NaH (20.0 g, 0.83 mol) at room temperature under nitrogen atmosphere and stirring. The addition of NaH was taken over 60 minutes. After the addition of NaH, the mixture was heated to 160° C. and kept at this temperature for 12 hours. After cooling, water (300.0 ml) was added into the reaction mixture. The product as a brown solid was collected by filtration. The crude product was purified with recrystallization from acetone/water to give 92.2 g (81.3 g) of product.

Workup

customat room temperature
waitkept at this temperature for 12 hours
temperatureAfter cooling
filtrationThe product as a brown solid was collected by filtration
customThe crude product was purified with recrystallization from acetone/water

Sources & evidence

ORD record: ord-f960f28bd3a7487b94423d29ee38a658
Source dataset: uspto-grants-2013_10
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US08546505B2

Reaction notes

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