Ammonium Hydroxide → HCID 10787443, compound

HRID 1251490Notes

Reaction equation

HRID 1251490 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 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)+=405.10; calculated, 405.10.

Workup

  1. additionwas added until the mixture
  2. extractionThe mixture was extracted with ethyl acetate
  3. customThe extract was evaporated
  4. customchromatographed on silica gel with 70:30 hexane-ethyl acetate

Sources & evidence

ORD record
ord-7b986c5e3b714e3c88365088f91f1546
Source dataset
uspto-grants-2002_01
Patent number
US06342503B1

Reaction notes

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