Nitrogen → HCID 12887440, compound
Reaction equation
Cl.[CH2:2]([O:4][C:5](=[O:8])[CH2:6]N)[CH3:3].CC1(C)[C:14]([CH3:16])(C)[O:13]BO1.C[CH2:19][N:20]([CH2:23]C)CC.N#N.C1(C2C=CC=CC=2)C=CC=CC=1P(C1CCCCC1)C1CCCCC1.[O:52]1CCOCC1>CC([O-])=O.CC([O-])=O.[Pd+2]>[CH2:14]([O:13][C:19]([NH:20][CH2:23][CH2:6][C:5]([O:4][CH2:2][CH3:3])=[O:8])=[O:52])[CH3:16]Participants
Reactant 6
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 80 °C
Procedure
A solution of compound b (77 g, 0.22 mol), 4,4,5,5-tetramethyl-[1,3,2]dioxaborolane (57 g, 0.44 mol) and Et3N (92 mL, 0.66 mol) in dioxane (500 mL) was purged with N2 for 30 minutes. Then Pd(OAc)2 (2.7 g, 0.011 mol) and biphenyl-2-yl-dicyclohexyl-phosphane (8.5 g, 0.022 mol) were added to the resulting mixture. After the addition, the reaction mixture was stirred at 80° C. for 1.5 hours. TLC (petroleum ether/EtOAc 30:1) indicated complete consumption of compound b. The resulting mixture was washed with saturated NH4Cl (500 mL), H2O (500 mL) and brine (500 mL) in sequence, dried over Na2SO4 and concentrated in vacuo to give crude compound c, which was purified by column chromatography (silica gel, petroleum ether/EtOAc from 5:1 to 1:1) to yield pure compound c (35 g, yield: 45%) as a brown solid.
Workup
- additionAfter the addition
- customconsumption of compound b
- washThe resulting mixture was washed with saturated NH4Cl (500 mL), H2O (500 mL) and brine (500 mL) in sequence
- dry with materialdried over Na2SO4
- concentrationconcentrated in vacuo
Sources & evidence
- ORD record
- ord-878b63313df84d4ca0677560d4643b03
- Source dataset
- uspto-grants-2011_12
- Patent number
- US08080556B2
Reaction notes
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