4-Nitro-1H-indole → HCID 59743448, compound

HRID 1946983Notes

Reaction equation

HRID 1946983 reaction equation
CC(C)=O.C(=O)=O.[N+:8]([C:11]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:12]=1[CH:13]=[CH:14][NH:15]2)([O-:10])=[O:9].Cl[C:21]1([S:27][CH3:28])C=CN=[CH:23][NH:22]1.[C:29](#[N:31])[CH3:30].C1COCC1>>[CH3:28][S:27][C:21]1[N:22]=[C:23]([N:15]2[C:16]3[C:12](=[C:11]([N+:8]([O-:10])=[O:9])[CH:19]=[CH:18][CH:17]=3)[CH:13]=[CH:14]2)[CH:30]=[CH:29][N:31]=1

Participants

5

Reactant 4

HCID 1457664-Nitro-1H-indoleHCID 18522661Acetone cardiceHCID 22177404Acetonitrile tetrahydrofuranHCID 178503302HCID 178503302, compound

Product 1

HCID 59743448HCID 59743448, compound

Procedure

A solution of sodium(bistrimethylsilyl)amide (1 M in THF, 26.42 mL) was slowly added to a cooled (acetone/dry-ice bath) solution of 4-nitroindole (4.2 g, 25.9 mmol) in a mixture of acetonitrile/THF (2/1, 75 mL) and the resulting mixture was stirred for 1 hour. 4-Chloro-4-methylthiopyrimidine (4.202 g, 26.2 mmol) was then added and the reaction mixture was warmed to RT and stirred for 21 h. The resulting mixture was evaporated under reduced pressure and the solid residue was triturated with a mixture of hexane/EtOAc/Et2O (5/1/1). The solid was collected by filtration, washed and dried under reduced pressure to give 2.56 g of 1-(2-methylsulfanyl-pyrimidin-4-yl)-4-nitro-1H-indole which was used without further purification.

Workup

  1. stirringstirred for 21 h
  2. customThe resulting mixture was evaporated under reduced pressure
  3. customthe solid residue was triturated with a mixture of hexane/EtOAc/Et2O (5/1/1)
  4. filtrationThe solid was collected by filtration
  5. washwashed
  6. customdried under reduced pressure

Sources & evidence

ORD record
ord-5c22413d67574e5d8c1a7a09bea04414
Source dataset
uspto-grants-2013_03
Patent number
US08399462B2

Reaction notes

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