Methanol → HCID 15767451, compound

HRID 1599064Notes

Reaction equation

HRID 1599064 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][NH:6]2.[H-].[Na+].Cl[C:14]1[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:23])[F:22])=[CH:16][N:15]=1.CO>CN(C)C=O>[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[CH:4]=[CH:5][N:6]2[C:14]1[C:19]([Cl:20])=[CH:18][C:17]([C:21]([F:24])([F:22])[F:23])=[CH:16][N:15]=1

Participants

6

Reactant 4

HCID 887MethanolHCID 24758Sodium hydrideHCID 1122342,3-Dichloro-5-(trifluoromethyl)pyridineHCID 5834314-Aminoindole

Product 1

HCID 15767451HCID 15767451, compoundYield 47.4%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

4-Aminoindole (5.8 g, 44 mmol) and sodium hydride (80% dispersion in mineral oil, 1.3 g, 44 mmol) were stirred together in N,N-dimethylformamide (60 ml), with ice-bath cooling for 5 minutes, and then 2,3-dichloro-5-trifluoromethylpyridine (5,8 g, 44 mmol) was added slowly. The mixture was stirred at room temperature for 18 hours, and then a small quantity of methanol was added. The mixture was partitioned between diethyl ether and water. The ethereal solution was dried over magnesium sulfate, filtered and the filtrate evaporated in vacuo to give 4-amino-1-(3'-chloro-5'-trifluoromethylpyridin-2-yl)indole (6.5 g) as a dark solid.

Workup

  1. temperaturecooling for 5 minutes
  2. customThe mixture was partitioned between diethyl ether and water
  3. dry with materialThe ethereal solution was dried over magnesium sulfate
  4. filtrationfiltered
  5. customthe filtrate evaporated in vacuo

Sources & evidence

ORD record
ord-7dbd70a9e09d4af6abb855c2112b706f
Source dataset
uspto-grants-1998_04
Patent number
US05739353

Reaction notes

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