HCID 59191203, compound → HCID 59191279, compound

HRID 1023906Notes

Reaction equation

HRID 1023906 reaction equation
Br[C:2]1[CH:15]=[CH:14][C:5]([O:6][C:7]2[CH:12]=[CH:11][CH:10]=[C:9]([F:13])[N:8]=2)=[C:4]([O:16][CH3:17])[CH:3]=1.[Br-].[CH2:19]([Zn+])[CH:20]([CH3:22])[CH3:21]>C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:13][C:9]1[CH:10]=[CH:11][CH:12]=[C:7]([O:6][C:5]2[CH:14]=[CH:15][C:2]([CH2:19][CH:20]([CH3:22])[CH3:21])=[CH:3][C:4]=2[O:16][CH3:17])[N:8]=1

Participants

4

Reactant 2

HCID 59191203HCID 59191203, compoundHCID 178448254HCID 178448254, compound

Product 1

HCID 59191279HCID 59191279, compoundYield 20%

Reagents, catalysts & solvents 1

HCID 178418397HCID 178418397, compoundCatalyst

Conditions

Temperature
105 °C

Procedure

To a suspension of Pd(PPh3)4 (0.025 mmol; 17 mg) under argon, in anhydrous, degased dioxane (2 mL), sheltered from light, were added 2-(4-bromo-2-methoxyphenoxy)-6-fluoropyridine (0.51 mmol; 151 mg), then isobutyl zinc bromide (1.0 mmol; 2.0 mL). The reaction was heated to 105° C. for 24 hr. The mixture was then hydrolysed with water (3 mL), extracted with ethyl acetate (3*3 mL). Combined organic phases were dried over MgSO4, concentrated under reduced pressure. The crude was then purified by preparative chromatography (cyclohexane/dichloromethane) to yield the desired product as a clear oil (28 mg; 0.10 mmol; 20%).

Workup

  1. customin anhydrous, degased dioxane (2 mL)
  2. extractionhydrolysed with water (3 mL), extracted with ethyl acetate (3*3 mL)
  3. dry with materialCombined organic phases were dried over MgSO4
  4. concentrationconcentrated under reduced pressure
  5. customThe crude was then purified by preparative chromatography (cyclohexane/dichloromethane)

Sources & evidence

ORD record
ord-c27a6308980b40bf9851873af6a92cfc
Source dataset
uspto-grants-2014_05
Patent number
US08722746B2

Reaction notes

Loading…