Pyridine → HCID 86725330, compound

HRID 925217Notes

Reaction equation

HRID 925217 reaction equation
[CH2:1]([O:3][C:4]([N:6]1[CH2:23][CH2:22][C:10]2[C:11]3[C:12](O)([CH3:20])[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].N1C=CC=CC=1.O=S(Cl)[Cl:32]>>[CH2:1]([O:3][C:4]([N:6]1[CH2:23][CH2:22][C:10]2[C:11]3[C:12]([Cl:32])([CH3:20])[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

4

Reactant 3

HCID 1049PyridineHCID 24386Thionyl ChlorideHCID 86725331HCID 86725331, compound

Product 1

HCID 86725330HCID 86725330, compound

Conditions

Temperature
50 °C

Procedure

Into a glass vial containing the product from step (a) (231 mg, 0.710 mmol) dissolved in SOCl2 (2 ml), pyridine (1 μL, 0.0071 mmol) was added. The stirred reaction mixture was heated to 50° C. for 30 minutes. The volatiles were evaporated in vacuo and the residue diluted with water (50 ml). The aqueous mixture was extracted with EtOAc (3×). The combined EtOAc extracts were washed with brine, dried over Na2SO4, and solvent evaporated in vacuo to give the sub-title compound as a dark yellow oil (214 mg) that was used without further purification. MS: ESI (positive): 344 (M+1).

Workup

  1. customThe stirred reaction mixture
  2. customThe volatiles were evaporated in vacuo
  3. additionthe residue diluted with water (50 ml)
  4. extractionThe aqueous mixture was extracted with EtOAc (3×)
  5. washThe combined EtOAc extracts were washed with brine
  6. dry with materialdried over Na2SO4, and solvent
  7. customevaporated in vacuo

Sources & evidence

ORD record
ord-4e946bf124194e16a27d81288b4929c6
Source dataset
uspto-grants-2016_03
Patent number
US09284277B2

Reaction notes

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