Pyridine → HCID 86725325, compound

HRID 925212Notes

Reaction equation

HRID 925212 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:28][CH2:27][C:10]2[C:11]3[C:12](O)([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[C:13]([F:19])([F:18])[CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2].S(Br)([Br:31])=O.N1C=CC=CC=1>ClCCCl>[CH2:1]([O:3][C:4]([N:6]1[CH2:28][CH2:27][C:10]2[C:11]3[C:12]([Br:31])([C:20]4[CH:21]=[N:22][CH:23]=[CH:24][CH:25]=4)[C:13]([F:19])([F:18])[CH2:14][C:15]=3[CH:16]=[CH:17][C:9]=2[CH2:8][CH2:7]1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 1049PyridineHCID 68176Thionyl bromideHCID 86725326HCID 86725326, compound

Product 1

HCID 86725325HCID 86725325, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
70 °C

Procedure

Into a 500 ml flask containing the product from step (a) (5.9 g, 15.20 mmol) in DCE (50 ml), thionyl bromide (5.89 ml, 76.03 mmol) was added, followed by pyridine (123 μL, 1.52 mmol). The stirred reaction mixture was heated to 70° C. for 30 minutes. The reaction mixture was then allowed to cool to room temperature and was carefully poured over ice-cold saturated aqueous Na2CO3 and extracted with DCM (3×). The combined DCM extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the sub-title compound as a pale red semi-solid that was used without further purification. MS: ESI (positive): 451, 453 (M+1).

Workup

  1. additionwas added
  2. customThe stirred reaction mixture
  3. temperatureto cool to room temperature
  4. additionwas carefully poured over ice-cold saturated aqueous Na2CO3
  5. extractionextracted with DCM (3×)
  6. washThe combined DCM extracts were washed with brine
  7. dry with materialdried over Na2SO4, and solvent
  8. customevaporated in vacuo

Sources & evidence

ORD record
ord-da5d0cc0adac42008c9df469285b8fbb
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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