Triphenylphosphine → 2-[3-(3,5-Dimethylpyrazol-1-yl)-phenoxy]-carbazole

HRID 1509647Notes

Reaction equation

HRID 1509647 reaction equation
[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:13]=[CH:12][CH:11]=[C:10]([O:14][C:15]3[CH:20]=[CH:19][C:18]([C:21]4[CH:26]=[CH:25][CH:24]=[CH:23][C:22]=4[N+:27]([O-])=O)=[CH:17][CH:16]=3)[CH:9]=2)[N:3]=1.C1C=CC(P(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>ClC1C=CC=CC=1Cl>[CH3:1][C:2]1[CH:6]=[C:5]([CH3:7])[N:4]([C:8]2[CH:9]=[C:10]([CH:11]=[CH:12][CH:13]=2)[O:14][C:15]2[CH:20]=[CH:19][C:18]3[C:21]4[C:22](=[CH:23][CH:24]=[CH:25][CH:26]=4)[NH:27][C:17]=3[CH:16]=2)[N:3]=1

Participants

4

Reactant 2

HCID 11776TriphenylphosphineHCID 1177297763,5-dimethyl-1-(3-(2'-nitrobiphenyl-4-yloxy)phenyl)-1H-pyrazole

Product 1

HCID 681812542-[3-(3,5-Dimethylpyrazol-1-yl)-phenoxy]-carbazoleYield 92%

Reagents, catalysts & solvents 1

HCID 72391,2-DichlorobenzeneSolvent

Procedure

A solution of 3,5-dimethyl-1-(3-(2′-nitrobiphenyl-4-yloxy)phenyl)-1H-pyrazole 3 (2.19 g, 5.68 mmol, 1.0 eq) and PPh3 (4.47 g, 17.04 mmol, 3.0 eq) in 1,2-dichlorobenzene (30 mL) was refluxed (175-185° C.) for 24 hours, then cooled, and 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) as an eluent to obtain the desired product as a white solid (1.83 g in 92% yield). 1H NMR (DMSO-d6, 400 MHz): δ 2.11 (s, 3H), 2.28 (s, 3H), 6.02 (s, 1H), 6.92 (dd, J=8.4, 2.0 Hz, 1H), 7.05 (dd, J=8.4, 2.4 Hz, 1H), 7.10 (t, J=2.0 Hz, 1H), 7.13-7.16 (m, 2H), 7.22-7.25 (m, 1H), 7.32-7.36 (m, 1H), 7.46 (d, J=8.0, 1H), 7.47 (t, J=8.4 Hz, 1H), 8.07 (d, J=7.2 Hz, 1H), 8.12 (d, J=8.4 Hz, 1H), 11.25 (s, 1H). 13C NMR (DMSO-d6, 100 MHz): δ 12.30, 13.24, 101.46, 107.52, 110.92, 111.10, 113.37, 116.43, 118.09, 118.87, 119.12, 119.88, 121.50, 122.23, 125.23, 130.36, 139.24, 140.17, 140.68, 140.99, 148.10, 154.44, 158.21.

Workup

  1. temperaturecooled
  2. customthe solvent was removed by distillation under high vacuum
  3. customThe residue was purified through column chromatography on silica gel

Sources & evidence

ORD record
ord-2ed157f85cfc4c188c665f69ae05ea06
Source dataset
uspto-grants-2015_12
Patent number
US09224963B2

Reaction notes

Loading…