Acetic Anhydride → N-(1-(5-Bromo-3-fluoropyridin-2-yl)vinyl)acetamide
Reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([C:8]#[N:9])=[N:6][CH:7]=1.[CH3:11][Mg]Cl.[C:14](OC(=O)C)(=[O:16])[CH3:15]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[C:4]([F:10])[C:5]([C:8]([NH:9][C:14](=[O:16])[CH3:15])=[CH2:11])=[N:6][CH:7]=1Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- -10 °C
Procedure
Compound of Step 3 (1 eq) was dissolved in toluene (10 vol). The batch was cooled to −10° C. and MeMgCl (1.5 eq) was added maintaining the temperature<0° C. The mixture was aged for 1 h and acetic anhydride was added over approximately 30 min maintaining the temperature<0° C. The reaction was aged for 18 h at −10° C. The mixture was quenched with half-saturated NaHCO3 (6 vol) and aged at 20-25° C. for 30 min. The layers were separated and the organic layer was washed with water (5 vol), 10% aqueous Na2SO4 (2×5 vol) and water (2×5 vol). The batch was concentrated under vacuum to give the title compound.
Workup
- temperaturemaintaining the temperature<0° C
- temperaturemaintaining the temperature<0° C
- waitThe reaction was aged for 18 h at −10° C
- customThe mixture was quenched with half-saturated NaHCO3 (6 vol)
- waitaged at 20-25° C. for 30 min
- customThe layers were separated
- washthe organic layer was washed with water (5 vol), 10% aqueous Na2SO4 (2×5 vol) and water (2×5 vol)
- concentrationThe batch was concentrated under vacuum
Sources & evidence
- ORD record
- ord-306d18aaeaa04856ae58205d6570c0c3
- Source dataset
- uspto-grants-2010_09
- Patent number
- US07790754B2
Reaction notes
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