Pyridine → HCID 68074936, compound

HRID 2040026Notes

Reaction equation

HRID 2040026 reaction equation
[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[N:16]=[C:15](O)[O:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1.N1C=CC=CC=1.O=P(Cl)(Cl)[Cl:26]>>[Br:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2([C:12]3[N:16]=[C:15]([Cl:26])[O:14][N:13]=3)[CH2:11][CH2:10][CH2:9]2)=[CH:4][CH:3]=1

Participants

4

Reactant 3

HCID 1049PyridineHCID 24813Phosphorus oxychlorideHCID 178517393HCID 178517393, compound

Product 1

HCID 68074936HCID 68074936, compoundYield 59.5%

Conditions

Temperature
90 °C

Procedure

To a solution of R109 (500 mg, 1.694 mmol) in pyridine (1.618 mL, 20 mmol) is added POCl3 (1.551 mL, 16.94 mmol) in a pressure flask. The reaction mixture is stirred at 90° C. for 18 hours. After this time, the reaction mixture is poured into ice water and extracted with EA twice. The organics are combined and washed with brine, dried over Na2SO4, filtered and concentrated in vacuo. The crude is purified by flash chromatography (SiO2, 5-40% EA/Heptane) to afford the title compound (316 mg); no ionization.

Workup

  1. extractionextracted with EA twice
  2. washwashed with brine
  3. dry with materialdried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude is purified by flash chromatography (SiO2, 5-40% EA/Heptane)

Sources & evidence

ORD record
ord-8f3b11b386e94a0e8216bd96019cd1a4
Source dataset
uspto-grants-2013_11
Patent number
US08580829B2

Reaction notes

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