1,4-Dioxane → HCID 67026923, compound

HRID 2040786Notes

Reaction equation

HRID 2040786 reaction equation
[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[CH:9][N:8]=[C:7](Cl)[CH:6]=1)[CH3:2].[Cl-].[CH:14]1([Zn+])[CH2:18][CH2:17][CH2:16][CH2:15]1.O1CCOC[CH2:21]1>O>[CH2:1]([O:3][C:4](=[O:12])[C:5]1[CH:10]=[C:9]([CH3:21])[N:8]=[C:7]([CH:14]2[CH2:18][CH2:17][CH2:16][CH2:15]2)[CH:6]=1)[CH3:2]

Participants

5

Reactant 3

HCID 312751,4-DioxaneHCID 2762942Ethyl 2-chloroisonicotinateHCID 178479836HCID 178479836, compound

Product 1

HCID 67026923HCID 67026923, compound

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
75 °C

Procedure

Under argon, Pd(dppf) (200 mg, 0.245 mmol) is added to a solution of 2-chloro-isonicotinic acid ethyl ester (4.80 g, 24.0 mmol) in dioxane (60 mL). A solution of cyclopentyl zinc chloride (50 mL, 24.0 mmol, ˜2 M solution in THF) is added dropwise. The mixture is stirred at 75° C. for 2 h before it is cooled to rt, carefully diluted with water and extracted twice with EA. The combined org. extracts are dried over MgSO4, filtered and concentrated. The crude product is purified by CC on silica gel eluting with heptane:EA 9:1 to give 2-cyclopentyl-6-methyl-isonicotinic acid ethyl ester (3.96 g) as an oil; LC-MS: tR=0.72 min, [M+1]+=234.11.

Workup

  1. temperatureis cooled to rt
  2. extractionextracted twice with EA
  3. dry with materialextracts are dried over MgSO4
  4. filtrationfiltered
  5. concentrationconcentrated
  6. customThe crude product is purified by CC on silica gel eluting with heptane:EA 9:1

Sources & evidence

ORD record
ord-435ddfb68c4e4092b4c58f53aadb122b
Source dataset
uspto-grants-2013_11
Patent number
US08580824B2

Reaction notes

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