Ethanol → 5-Methyl-2-(2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenylamine

HRID 1262351Notes

Reaction equation

HRID 1262351 reaction equation
[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]3[C:11]([CH:12]=[N:13][C:14]([S:17][CH3:18])=[N:15]3)=[CH:10][CH:9]=2)=[C:4]([N+:19]([O-])=O)[CH:3]=1.[Cl-].[NH4+].C(O)C.O>[Fe]>[CH3:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:16]3[C:11]([CH:12]=[N:13][C:14]([S:17][CH3:18])=[N:15]3)=[CH:10][CH:9]=2)=[C:4]([NH2:19])[CH:3]=1

Participants

6

Reactant 4

HCID 702EthanolHCID 962WaterHCID 25517Ammonium ChlorideHCID 667120777-(4-Methyl-2-nitro-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine

Product 1

HCID 667127275-Methyl-2-(2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenylamineYield 88%

Reagents, catalysts & solvents 1

HCID 23925IronCatalyst

Conditions

Temperature
100 °C

Procedure

A mixture of 7-(4-Methyl-2-nitro-phenyl)-2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazine (620 mg, 2.1 mmol), iron (346 mg, 6.19 mmol), ammonium chloride (55.2 mg, 1.03 mmol) in ethanol (12.0 mL, 206 mmol) and water (8 mL, 400 mmol) was heated at 100° C. The mixture was cooled, solvent was evaporated and was diluted with water and EtOAc. It was filtered through a pad of celite, extracted from EtOAc, combined organic was washed with brine. After drying, solvent was evaporated to give 5-Methyl-2-(2-methylsulfanyl-pyrrolo[2,1-f][1,2,4]triazin-7-yl)-phenylamine as a solid (491 mg, 88%). LCMS (E/I+) 271. The product was taken to the next step without further purification.

Workup

  1. temperatureThe mixture was cooled
  2. customsolvent was evaporated
  3. additionwas diluted with water and EtOAc
  4. filtrationIt was filtered through a pad of celite
  5. extractionextracted from EtOAc
  6. washcombined organic was washed with brine
  7. customAfter drying
  8. customsolvent was evaporated

Sources & evidence

ORD record
ord-0b1e34e603ba4b4c9eef3e320322bfb6
Source dataset
uspto-grants-2013_06
Patent number
US08471005B2

Reaction notes

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