Carbazole → HCID 58013136, compound

HRID 1625654Notes

Reaction equation

HRID 1625654 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.I[C:15]1[CH:16]=[C:17]([C:21]2[CH:26]=[CH:25][C:24](I)=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=1.C([O-])([O-])=O.[K+].[K+].C1O[CH2:50][CH2:49]OCCOCCOCCOCCOC1>ClC1C=CC=CC=1Cl.[Cu]>[C:17]1([C:21]2[CH:26]=[CH:25][C:24]([N:12]3[C:50]4[CH:49]=[CH:2][CH:3]=[CH:4][C:5]=4[C:6]4[C:11]3=[CH:10][CH:9]=[CH:8][CH:7]=4)=[CH:23][CH:22]=2)[CH:18]=[CH:19][CH:20]=[C:15]([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:16]=1

Participants

7

Reactant 4

HCID 6854CarbazoleHCID 11430Potassium CarbonateHCID 2855718-Crown-6HCID 12794771HCID 12794771, compound

Product 1

HCID 58013136HCID 58013136, compoundYield 69.7%

Reagents, catalysts & solvents 2

HCID 23978CopperCatalystHCID 72391,2-DichlorobenzeneSolvent

Procedure

Carbazole (0.90 g, 5.42 mmol), 3,4′-diiodobiphenyl, K2CO3 (2.72 g, 19.7 mmol), copper powder (0.43 g, 6.77 mmol), and 18-crown-6 (0.13 g, 0.49 mmol) were dissolved in o-dichlorobenzene and heated to reflux for 48 h. The solution was filtered and the solvent removed in vacuo, the residue was recrystallized from MeOH to afford the product (0.83 g, 69.7%). 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. temperatureheated
  2. temperatureto reflux for 48 h
  3. filtrationThe solution was filtered
  4. customthe solvent removed in vacuo
  5. customthe residue was recrystallized from MeOH

Sources & evidence

ORD record
ord-b6d63de21abc4e3f85c2b2963f4013ed
Source dataset
uspto-grants-2014_07
Patent number
US08785002B1

Reaction notes

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