2-Chloroethyl methyl sulfide → HCID 58542155, compound

HRID 237427Notes

Reaction equation

HRID 237427 reaction equation
[CH2:1]([S:4][C:5]1[N:10]=[C:9]([N:11]2[C:19]3[CH:18]=[CH:17][CH:16]=[C:15]([OH:20])[C:14]=3[CH:13]=[N:12]2)[CH:8]=[CH:7][N:6]=1)[CH2:2][CH3:3].C(=O)([O-])[O-].[K+].[K+].Cl[CH2:28][CH2:29][S:30][CH3:31].CN1C(=O)CCC1>O>[CH3:31][S:30][CH2:29][CH2:28][O:20][C:15]1[CH:16]=[CH:17][CH:18]=[C:19]2[C:14]=1[CH:13]=[N:12][N:11]2[C:9]1[CH:8]=[CH:7][N:6]=[C:5]([S:4][CH2:1][CH2:2][CH3:3])[N:10]=1

Participants

6

Reactant 4

HCID 109652-Chloroethyl methyl sulfideHCID 11430Potassium CarbonateHCID 13387N-methyl-2-pyrrolidoneHCID 136197463HCID 136197463, compound

Product 1

HCID 58542155HCID 58542155, compoundYield 93.3%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
80 °C

Procedure

1-(2-Propylsulfanyl-pyrimidin-4-yl)-1H-indazol-4-ol (600 mg), potassium carbonate (1.104 g) and 1-chloro-2-methylsulfanyl-ethane 401.9 mg) were added to NMP (6 mL), and the mixture was heated to 80° C. for three hours. The mixture was cooled, diluted with water and filtered. The collected solid was washed with water and dried under reduced pressure to give 705 mg of 4-(2-Methylsulfanyl-ethoxy)-1-(2-propylsulfanyl-pyrimidin-4-yl)-1H-indazole.

Workup

  1. temperatureThe mixture was cooled
  2. filtrationfiltered
  3. washThe collected solid was washed with water
  4. customdried under reduced pressure

Sources & evidence

ORD record
ord-a52cdd5682af485c8241a27909ebcad1
Source dataset
uspto-grants-2014_02
Patent number
US08642601B2

Reaction notes

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