Ammonium Hydroxide → HCID 10787443, compound

HRID 1872045Notes

Reaction equation

HRID 1872045 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]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:16]=[C:17]([CH3:20])[N:18]=2)[C:13](C#N)=[CH:12]1.[OH-].[NH4+]>S(=O)(=O)(O)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]([C:21]3[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=3)[CH:16]=[C:17]([CH3:20])[N:18]=2)[CH:13]=[CH:12]1

Participants

4

Reactant 2

HCID 14923Ammonium HydroxideHCID 10502734HCID 10502734, compound

Product 1

HCID 10787443HCID 10787443, compoundYield 92%

Reagents, catalysts & solvents 1

HCID 1118Sulfuric AcidSolvent

Procedure

A mixture of 130 mg (0.302 mmole) of 1-(2-bromo-4-isopropylphenyl)-3-cyano-6-methyl-4-phenyl-7-azaindole (Example 66) and 10 mL of 65% sulfuric acid were refluxed for one hour. The mixture was poured onto ice. Conc. ammonium hydroxide was added until the mixture was basic to pH paper. The mixture was extracted with ethyl acetate. The extract was evaporated and chromatographed on silica gel with 70:30 hexane-ethyl acetate. There was obtained 112 mg (92% yield) of 1-(2-bromo-4-isopropylphenyl)-6-methyl-4-phenyl-7-azaindole. Mass spec: (M+H)+ =4.05.10; calculated, 405.10.

Workup

  1. temperaturewere refluxed for one hour
  2. additionThe mixture was poured onto ice
  3. extractionThe mixture was extracted with ethyl acetate
  4. customThe extract was evaporated
  5. customchromatographed on silica gel with 70:30 hexane-ethyl acetate

Sources & evidence

ORD record
ord-ab267b62c6fd421b869e9d653a657987
Source dataset
uspto-grants-2000_08
Patent number
US06107301

Reaction notes

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