Pyridine → HCID 63379767, compound

HRID 58644Notes

Reaction equation

HRID 58644 reaction equation
[F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]([OH:6])=O.[C:12](Cl)(=[O:16])[C:13](Cl)=O.CN([CH:21]=[O:22])C.C([N:26]([CH2:30]C)C(C)C)(C)C.[N:32]1C=CC=CC=1>ClCCl>[F:1][C:2]1[CH:10]=[CH:9][C:8]([F:11])=[CH:7][C:3]=1[C:4]1[O:6][N:26]=[C:30]([C:21]([O:16][CH2:12][CH3:13])=[O:22])[N:32]=1

Participants

7

Reactant 5

HCID 1049PyridineHCID 6228DimethylformamideHCID 65578Oxalyl chlorideHCID 763392,5-Difluorobenzoic acidHCID 81531Diisopropylethylamine

Product 1

HCID 63379767HCID 63379767, compoundYield 36%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

This compound was prepared according to general method 2 with (step I) 2,5-difluorobenzoic acid (0.299 g; 1.89 mmol) and oxalyl chloride (0.176 mL; 2.08 mmol) in dichloromethane (12 mL) with few drops of DMF and (step II) ethyl 2-amino-2-(hydroxyimino) acetate (0.250 g; 1.89 mmol) and N,N diisopropylethylamine (0.527 mL; 3.03 mmol) in dichloromethane (10 mL) and (step III) pyridine (18 mL). The crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane) to yield 0.172 g (36%) of ethyl 5-(2,5-difluorophenyl)-1,2,4-oxadiazole-3-carboxylate as a white solid.

Workup

  1. customThis compound was prepared
  2. customThe crude material was purified by flash chromatography on silica (eluent 20 to 100% ethyl acetate in heptane)

Sources & evidence

ORD record
ord-87a30af8656f4b928f85829ca527739e
Source dataset
uspto-grants-2016_09
Patent number
US09434722B2

Reaction notes

Loading…