Phosphorus oxychloride → HCID 68089523, compound

HRID 539783Notes

Reaction equation

HRID 539783 reaction equation
Br.[F:2][C:3]1[CH:8]=[CH:7][CH:6]=[CH:5][C:4]=1[C:9]1[CH:14]=[CH:13][C:12](=[NH:15])[N:11]([CH2:16][C:17](OC)=O)[N:10]=1.O=P(Cl)(Cl)[Cl:23]>ClC1C=CC=CC=1>[Cl:23][C:17]1[N:15]=[C:12]2[CH:13]=[CH:14][C:9]([C:4]3[CH:5]=[CH:6][CH:7]=[CH:8][C:3]=3[F:2])=[N:10][N:11]2[CH:16]=1

Participants

4

Reactant 2

HCID 24813Phosphorus oxychlorideHCID 68089040HCID 68089040, compound

Product 1

HCID 68089523HCID 68089523, compoundYield 85.5%

Reagents, catalysts & solvents 1

HCID 7964ChlorobenzeneSolvent

Conditions

Temperature
120 °C

Procedure

To a solution of methyl 2-(3-(2-fluorophenyl)-6-iminopyridazin-1(6H)-yl)acetate hydrobromide (0.5 g, 1.46 mmol) in chlorobenzene (20 mL) is added POCl3 (7.30 mmol). The reaction mixture is heated at 120° C. for 4 hours, cooled, concentrated under reduced pressure to dryness and sat. aqueous NaHCO3 (25 mL) is added. The mixture is extracted with CH2Cl2 (3×20 mL). Organic layer is collected, dried over Na2SO4, filtered and concentrated to dryness. The crude product is purified via silica chromatography (hexanes to EtOAc) to afford the title compound (0.309 g, 85%) as a white solid: Rf 0.39 (1:4 EtOAc:hexanes); LCMS (m/z)=248.2, 250.2 [M+H]+, tR=2.51 min.

Workup

  1. temperaturecooled
  2. concentrationconcentrated under reduced pressure to dryness and sat. aqueous NaHCO3 (25 mL)
  3. additionis added
  4. extractionThe mixture is extracted with CH2Cl2 (3×20 mL)
  5. customOrganic layer is collected
  6. dry with materialdried over Na2SO4
  7. filtrationfiltered
  8. concentrationconcentrated to dryness
  9. customThe crude product is purified via silica chromatography (hexanes to EtOAc)

Sources & evidence

ORD record
ord-8a8d0bca9e80414c8bcab928e46d87dd
Source dataset
uspto-grants-2014_10
Patent number
US08871767B2

Reaction notes

Loading…