O-Xylene → HCID 10737736, compound

HRID 1872044Notes

Reaction equation

HRID 1872044 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]1[C:19]2[C:14](=[C:15]([CH3:21])[CH:16]=[C:17]([CH3:20])[N:18]=2)[C:13]([C:22]#[N:23])=[CH:12]1.[C:24]1(C)[C:25](C)=[CH:26]C=[CH:28][CH:29]=1>O>[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]1[C:19]2[C:14](=[C:15]([CH3:21])[CH:16]=[C:17]([C:20]3[CH:26]=[CH:25][CH:24]=[CH:29][CH:28]=3)[N:18]=2)[C:13]([C:22]#[N:23])=[CH:12]1.[Br:1][C:2]1[CH:7]=[C:6]([CH:8]([CH3:10])[CH3:9])[CH:5]=[CH:4][C:3]=1[N:11]1[C:19]2[C:14](=[C:15]([CH3:21])[CH:16]=[C:17]([CH3:20])[N:18]=2)[C:13]([C:22]#[N:23])=[CH:12]1

Participants

5

Reactant 2

HCID 7237O-XyleneHCID 10737736HCID 10737736, compound

Product 2

HCID 10737736HCID 10737736, compoundHCID 10741267HCID 10741267, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Procedure

A mixture of 737 mg (2.00 mmole) of the product from Example 64 (Part B), 324 mg (2.00 mmole) of benzolyacetone and 25 mL of xylene was heated in a flask equipped with a water separator for 2 hours. The solvent was removed by evaporation, and the residue chromatographed on silica gel, eluting in step gradients with 0, 5, 10, and 15% ethyl acetate in hexane. Both 1-(2-bromo-4-isopropylphenyl)-3-cyano-4-methyl-6-phenyl-7-azaindole and 1-(2-bromo-4-isopropylphenyl)-3-cyano-6-methyl-4-methyl-7-azaindole were obtained. The Rf values were respectively 0.38 and 0.28 (silica gel with 80:20 hexane-ethyl acetate). The assignment of the structures was based on the nmr data of the de-cyanylated compounds in Example 67.

Workup

  1. temperaturewas heated in a flask
  2. customThe solvent was removed by evaporation
  3. customthe residue chromatographed on silica gel
  4. washeluting in step gradients with 0, 5, 10, and 15% ethyl acetate in hexane

Sources & evidence

ORD record
ord-abe6df4f74534bbdaf45789412cd8393
Source dataset
uspto-grants-2000_08
Patent number
US06107301

Reaction notes

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