Phosphorus oxychloride → HCID 59832231, compound

HRID 269517Notes

Reaction equation

HRID 269517 reaction equation
CO[CH:3](OC)[CH2:4][N:5]([CH3:24])[C:6]([C:8]1[NH:9][CH:10]=[C:11]([C:13](=[O:23])[CH2:14][C:15]2[CH:20]=[CH:19][CH:18]=[C:17]([F:21])[C:16]=2[F:22])[CH:12]=1)=[O:7].O=P(Cl)(Cl)Cl.C(Cl)Cl.CO>O1CCOCC1>[F:22][C:16]1[C:17]([F:21])=[CH:18][CH:19]=[CH:20][C:15]=1[CH2:14][C:13]([C:11]1[C:12]2[CH:3]=[CH:4][N:5]([CH3:24])[C:6](=[O:7])[C:8]=2[NH:9][CH:10]=1)=[O:23]

Participants

5

Reactant 3

HCID 24813Phosphorus oxychlorideHCID 21226129Dichloromethane methanolHCID 59832228HCID 59832228, compound

Product 1

HCID 59832231HCID 59832231, compoundYield 41%

Reagents, catalysts & solvents 1

HCID 312751,4-DioxaneSolvent

Procedure

To 4-[(2,3-Difluoro-phenyl)-acetyl]-1H-pyrrole-2-carboxylic acid (2,2-dimethoxy-ethyl)-methyl-amide (200 mg, 0.55 mmol) in dioxane (50 mL) was added POCl3 (50 μL, 0.55 mmol) at 0C. The reaction solution was heated to 60C and stirred for 14 hr. The reaction was quenched with water and extracted with ethyl acetate, dried (Na2SO4). Flash chromatography (methylene chloride/methanol) gave 67 mg (41% yield)of title compound.

Workup

  1. customThe reaction was quenched with water
  2. extractionextracted with ethyl acetate
  3. dry with materialdried (Na2SO4)

Sources & evidence

ORD record
ord-6b442046a63f4c9ba03c72fefb020868
Source dataset
uspto-grants-2008_11
Patent number
US07446199B2

Reaction notes

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