HCID 10548172, compound → HCID 9998661, compound

HRID 1872046Notes

Reaction equation

HRID 1872046 reaction equation
[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[C:3]=1[N:12]1[C:20]2[C:15](=[C:16]([CH3:22])[CH:17]=[C:18]([CH3:21])[N:19]=2)[C:14](C#N)=[CH:13]1>S(=O)(=O)(O)O>[Br:1][C:2]1[CH:7]=[C:6]([O:8][CH3:9])[CH:5]=[C:4]([O:10][CH3:11])[C:3]=1[N:12]1[C:20]2[C:15](=[C:16]([CH3:22])[CH:17]=[C:18]([CH3:21])[N:19]=2)[CH:14]=[CH:13]1

Participants

3

Reactant 1

HCID 10548172HCID 10548172, compound

Product 1

HCID 9998661HCID 9998661, compoundYield 5.9%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 200 mg of 1-(2-bromo-4,6-dimethoxyphenyl)-3-cyano-4,6-dimethyl-7-azaindole and 10 ml of 65% sulfuric acid was refluxed for one hour. The mixture was worked up as described in Example 65 to give 185 mg of crude product. A 40 mg portion was purified by preparative liquid chromatography on a nitrile column using 95:5 1-chlorobutane-acetonitrile to give 11 mg of 1-(2-bromo-4,6-dimethoxyphenyl)-4,6-dimethyl-7-azaindole. Mass spec: (M+H)+ =360.9; calculated, 361.1.

Workup

  1. temperaturewas refluxed for one hour
  2. customto give 185 mg of crude product
  3. customA 40 mg portion was purified by preparative liquid chromatography on a nitrile column

Sources & evidence

ORD record
ord-b04214ccd42e4ac09cc430bdd9794ca5
Source dataset
uspto-grants-2000_08
Patent number
US06107301

Reaction notes

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