Triphenylphosphine → 2'-(pyridin-2-yl)-9H-2,9'-bicarbazole

HRID 1509635Notes

Reaction equation

[N+:1]([C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[CH:15]=[CH:14][C:13]([N:16]2[C:28]3[CH:27]=[C:26]([C:29]4[CH:34]=[CH:33][CH:32]=[CH:31][N:30]=4)[CH:25]=[CH:24][C:23]=3[C:22]3[C:17]2=[CH:18][CH:19]=[CH:20][CH:21]=3)=[CH:12][CH:11]=1)([O-])=O.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>ClC1C=CC=CC=1Cl>[N:30]1[CH:31]=[CH:32][CH:33]=[CH:34][C:29]=1[C:26]1[CH:25]=[CH:24][C:23]2[C:22]3[C:17](=[CH:18][CH:19]=[CH:20][CH:21]=3)[N:16]([C:13]3[CH:14]=[CH:15][C:10]4[C:5]5[C:4](=[CH:9][CH:8]=[CH:7][CH:6]=5)[NH:1][C:11]=4[CH:12]=3)[C:28]=2[CH:27]=1

Participants

Conditions

Temperature: 180 °C

Procedure

A solution of 9-(2′-nitrobiphenyl-4-yl)-2-(pyridin-2-yl)-9H-carbazole (1.00 g, 2.27 mmol, 1.0 eq) and PPh3 (2.38 g, 9.06 mmol, 4.0 eq) in 1,2-dichlorobenzene (15 mL) was stirred at refluxed temperature of 175-185° C. in an oil bath and for 46 hours under nitrogen, and cooled. The solvent was removed by distillation under high vacuum. The residue was purified through column chromatography on silica gel using hexane/ethyl acetate (10:1-5:1-3:1) as an eluent to obtain the desired product, 2′-(pyridin-2-yl)-9H-2,9′-bicarbazole, as a brown solid (814 g in 88% yield). 1H NMR (DMSO-d6, 400 MHz): δ 7.27 (t, J=8.0 Hz, 1H), 7.30-7.36 (m, 2H), 7.42 (dd, J=8.8, 1.2 Hz, 1H), 7.45-7.51 (m, 3H), 7.59 (d, J=8.8 Hz, 1H), 7.75 (d, J=1.6 Hz, 1H), 7.84-7.88 (m, 1H), 8.04 (d, J=8.4 Hz, 2H), 8.21 (s, 1H), 8.27 (d, J=8.0 Hz, 1H), 8.33 (d, J=7.2 Hz, 1H), 8.39 (d, J=7.6 Hz, 1H), 8.44 (d, J=8.8 Hz, 1H), 8.61 (d, J=4.8 Hz, 1H), 11.53 (s, 1H).

Workup

temperaturecooled
customThe solvent was removed by distillation under high vacuum
customThe residue was purified through column chromatography on silica gel

Sources & evidence

ORD record: ord-4fd0720009f8473eb0fb4171164e29ad
Source dataset: uspto-grants-2015_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US09224963B2

Reaction notes

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