Pyridine → HCID 178461802, compound

HRID 1455001Notes

Reaction equation

HRID 1455001 reaction equation
[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][S:6][C:7]1[N:12]=[C:11]([OH:13])[CH:10]=[C:9]([NH:14][C@H:15]([CH3:18])[CH2:16][OH:17])[N:8]=1.N1C=CC=CC=1.[S-:28][C:29]#[N:30].[K+].BrBr>CN(C=O)C>[Cl:1][C:2]1[CH:3]=[C:4]([CH:19]=[CH:20][CH:21]=1)[CH2:5][S:6][C:7]1[N:12]=[C:11]([OH:13])[C:10]([S:28][C:29]#[N:30])=[C:9]([NH:14][C@H:15]([CH3:18])[CH2:16][OH:17])[N:8]=1

Participants

6

Reactant 4

HCID 1049PyridineHCID 24408BromineHCID 516872Potassium thiocyanateHCID 178461795HCID 178461795, compound

Product 1

HCID 178461802HCID 178461802, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

The product of Example 3 (0.5 g), pyridine (0.21 ml) and potassium thiocyanate (0.6 g) were dissolved in DMF (10 ml) and cooled to 0° C. Bromine (74 μl) was added before the cooling bath was removed and the reaction mixture allowed to warm to room temperature. After 1 h water (50 ml) was added and the mixture extracted with EtOAc (3×30 ml). The combined extracts were dried (MgSO4), filtered, evaporated and purified by silica gel chromatography (10% methanol/DCM) to yield the title product as a white solid. Yield 0.3 g.

Workup

  1. customwas removed
  2. temperatureto warm to room temperature
  3. additionAfter 1 h water (50 ml) was added
  4. extractionthe mixture extracted with EtOAc (3×30 ml)
  5. dry with materialThe combined extracts were dried (MgSO4)
  6. filtrationfiltered
  7. customevaporated
  8. custompurified by silica gel chromatography (10% methanol/DCM)

Sources & evidence

ORD record
ord-ecedd9ed8c6745b8bb53939850ef782e
Source dataset
uspto-grants-2009_01
Patent number
US07482355B2

Reaction notes

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