Toluene → HCID 68091097, compound

HRID 923772Notes

Reaction equation

HRID 923772 reaction equation
[CH2:1]([S:3][C:4]1[CH:9]=[CH:8][CH:7]=[CH:6][C:5]=1[C:10]1[N:24]([CH3:25])[C:13]2=[N:14][CH:15]=[C:16]([CH:18](O)[C:19]([F:22])([F:21])[F:20])[CH:17]=[C:12]2[N:11]=1)[CH3:2].C1(C)C=CC=CC=1.S(Cl)([Cl:35])=O.C(=O)([O-])O.[Na+]>N1C=CC=CC=1>[Cl:35][CH:18]([C:16]1[CH:17]=[C:12]2[N:11]=[C:10]([C:5]3[CH:6]=[CH:7][CH:8]=[CH:9][C:4]=3[S:3][CH2:1][CH3:2])[N:24]([CH3:25])[C:13]2=[N:14][CH:15]=1)[C:19]([F:22])([F:21])[F:20]

Participants

6

Reactant 4

HCID 1140TolueneHCID 24386Thionyl ChlorideHCID 516892Sodium BicarbonateHCID 67981185HCID 67981185, compound

Product 1

HCID 68091097HCID 68091097, compound

Reagents, catalysts & solvents 1

HCID 1049PyridineSolvent

Conditions

Temperature
50 °C

Procedure

To a mixture of 1-[2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridin-6-yl]-2,2,2-trifluoro-ethanol (98 mg), toluene (10 ml), and pyridine (50 μl), thionyl chloride (1 ml) was added. The mixture was stirred with heating at 50° C. for 5 hours, and then saturated aqueous sodium hydrogen carbonate solution was poured, and extracted with ethyl acetate. The combined organic layer was dried over sodium, sulfate, and concentrated under reduced pressure. The residue was subjected to silica gel column chromatography to give 66 mg of 6-(1-chloro-2,2,2-trifluoro-ethyl)-2-(2-ethylsulfanyl-phenyl)-3-methyl-3H-imidazo[4,5-b]pyridine (hereinafter referred to as Present Compound 266).

Workup

  1. additionwas added
  2. extractionextracted with ethyl acetate
  3. dry with materialThe combined organic layer was dried over sodium, sulfate
  4. concentrationconcentrated under reduced pressure

Sources & evidence

ORD record
ord-ef686faa31c84875bbc42e616d28c786
Source dataset
uspto-grants-2016_03
Patent number
US09278983B2

Reaction notes

Loading…