Carbazole → HCID 58013136, compound

HRID 1625653Notes

Reaction equation

HRID 1625653 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.Br[C:15]1[CH:20]=[CH:19][C:18]([C:21]2[CH:26]=[CH:25][C:24](Br)=[CH:23][CH:22]=2)=[CH:17][CH:16]=1.[CH3:28][C:29]([CH3:32])([O-])[CH3:30].[K+]>C1(C)C=CC=CC=1>[C:18]1([C:21]2[CH:26]=[CH:25][C:24]([N:12]3[C:11]4[CH:10]=[CH:9][CH:8]=[CH:7][C:32]=4[C:29]4[C:30]3=[CH:2][CH:1]=[CH:13][CH:28]=4)=[CH:23][CH:22]=2)[CH:19]=[CH:20][CH:15]=[C:16]([N:12]2[C:11]3[CH:10]=[CH:9][CH:8]=[CH:7][C:6]=3[C:5]3[C:13]2=[CH:1][CH:2]=[CH:3][CH:4]=3)[CH:17]=1

Participants

5

Reactant 3

HCID 6854CarbazoleHCID 71104,4'-DibromobiphenylHCID 23665647Potassium tert-butoxide

Product 1

HCID 58013136HCID 58013136, compoundYield 6.9%

Reagents, catalysts & solvents 1

HCID 1140TolueneSolvent

Conditions

Temperature
135 °C

Procedure

Carbazole (1.80 g, 10.9 mmol), 4,4′-dibromobiphenyl (0.75 g, 2.4 mmol), and potassium tbutoxide (2.24 g, 20 mmol) were dissolved in dry toluene and heated at 135° C. for 24 h. The solution was filtered and the solvent was removed in vacuo, the residue was dry-packed on SiO2 and chromatographed using 10% acetone in hexanes to afford (0.08 g, 6%) of the product. 1H NMR (CDCl3) δ 8.22-8.16 (m, 4H), 7.93-7.65 (m, 8H), 7.56-7.49 (m, 8H), 7.47-7.28 (m, 4H). 13C NMR (CDCl3+DMSO-d6) δ 142.1, 140.8, 140.7, 139.0, 138.3, 137.3, 130.5, 128.5, 127.3, 126.1, 126.0, 125.9, 125.6, 123.4, 120.3, 120.2, 120.0, 109.7. EI MS m/z 484 [M+], m.p.=244-246° C.

Workup

  1. filtrationThe solution was filtered
  2. customthe solvent was removed in vacuo
  3. customchromatographed

Sources & evidence

ORD record
ord-15ac434f2d794cdc80d9a448a376691a
Source dataset
uspto-grants-2014_07
Patent number
US08785002B1

Reaction notes

Loading…