HCID 86663005, compound → HCID 66604959, compound

HRID 2410676Notes

Reaction equation

HRID 2410676 reaction equation
[N:1]([C:4]1[C:9]([C:10]#[N:11])=[CH:8][C:7]([C:12]2[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=2)=[CH:6][C:5]=1[C:20]1[CH:25]=[CH:24][C:23]([O:26][CH3:27])=[CH:22][CH:21]=1)=[N+]=[N-]>ClC1C=CC=CC=1Cl.CCCCCC>[CH3:27][O:26][C:23]1[CH:24]=[C:25]2[C:20]([C:5]3[CH:6]=[C:7]([C:12]4[CH:17]=[CH:16][C:15]([O:18][CH3:19])=[CH:14][CH:13]=4)[CH:8]=[C:9]([C:10]#[N:11])[C:4]=3[NH:1]2)=[CH:21][CH:22]=1

Participants

4

Reactant 1

HCID 86663005HCID 86663005, compound

Product 1

HCID 66604959HCID 66604959, compoundYield 72.4%

Reagents, catalysts & solvents 2

HCID 72391,2-DichlorobenzeneSolventHCID 8058HexaneSolvent

Procedure

A solution of 4′-azido-4,4″-dimethoxy-[1,1′:3′,1″-terphenyl]-5′-carbonitrile (108 mg, 0.303 mmol) in 1,2-dichlorobenzene (2 mL) was heated at 180° C. for 0.5 hr. It was allowed to cool to room temperature and diluted with hexane (about 5 mL). The precipitate was collected by filtration and washed with hexane to leave 7-methoxy-3-(4-methoxyphenyl)-9H-carbazole-1-carbonitrile (72 mg, 72% yield) as an off-white solid. MS (ESI) m/z 329.1 (M+H). 1H NMR (CDCl3) δ ppm 8.51 (1H, s), 8.28 (1H, s), 7.96 (1H, d, J=8.85 Hz), 7.76 (1H, d, J=1.83 Hz), 7.53-7.59 (2H, m), 7.00-7.04 (2H, m), 6.99 (1H, d, J=2.14 Hz), 6.93 (1H, dd, J=8.70, 2.29 Hz), 3.92 (3H, s), 3.87 (3H, s).

Workup

  1. filtrationThe precipitate was collected by filtration
  2. washwashed with hexane

Sources & evidence

ORD record
ord-d1277a78171844dc86546052a558694c
Source dataset
uspto-grants-2014_08
Patent number
US08815840B2

Reaction notes

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