Chloride → HCID 86746204, compound

HRID 466472Notes

Reaction equation

HRID 466472 reaction equation
[C:1]([CH2:3][C:4]1[C:5]([CH2:21][CH:22]2[CH2:24][CH2:23]2)=[C:6]([C:17]([O:19][CH3:20])=[O:18])[C:7]([CH:14]([F:16])[F:15])=[N:8][C:9]=1[C:10]([F:13])([F:12])[F:11])#[N:2].Br[CH2:26][CH2:27][CH2:28][C:29](Cl)=[O:30].[Cl-]>ClCCl.[OH-].[Na+]>[C:1]([C:3](=[C:29]1[CH2:28][CH2:27][CH2:26][O:30]1)[C:4]1[C:5]([CH2:21][CH:22]2[CH2:23][CH2:24]2)=[C:6]([C:17]([O:19][CH3:20])=[O:18])[C:7]([CH:14]([F:15])[F:16])=[N:8][C:9]=1[C:10]([F:13])([F:11])[F:12])#[N:2]

Participants

6

Reactant 3

HCID 312ChlorideHCID 702254-Bromobutyryl chlorideHCID 86746205HCID 86746205, compound

Product 1

HCID 86746204HCID 86746204, compoundYield 59%

Reagents, catalysts & solvents 2

HCID 6344DichloromethaneSolventHCID 14798Sodium HydroxideSolvent

Procedure

5(Cyanomethyl)-4-(cyclopropylmethyl)-2-(difluoromethyl)-6-(trifluoromethyl)-3-pyridinecarboxylic acid, methyl ester, prepared as in Example c, (3.0 g, 8.6 mmol) was reacted with 4.0 g (21.6 mmol) 4-bromobutyryl chloride in 160 mL dichloromethane and 82 mL 50% NaOH to which was added 0.3 g benezyltriethylammonium chloride. The solution was poured into 175 mL of ice water and extracted with ethyl ether. The organic layer was washed with water and brine and dried over magnesium sulfate. Purification by HPLC (30% EtOAc/hexane) yielded 2.1 g of the desired product as a light yellow oil, a 59% yield. nD25 1.5028.

Workup

  1. extractionextracted with ethyl ether
  2. washThe organic layer was washed with water and brine
  3. dry with materialdried over magnesium sulfate
  4. customPurification by HPLC (30% EtOAc/hexane)

Sources & evidence

ORD record
ord-cfc2d970d9af4d3190243390d4d8fc3f
Source dataset
uspto-grants-1992_10
Patent number
US05156670

Reaction notes

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