Dichloromethane → [6-(Dimethylcarbamoyl)pyridin-3-yl]boronic acid
Reaction equation
Br[C:2]1[CH:3]=[CH:4][C:5]([C:8]([N:10]([CH3:12])[CH3:11])=[O:9])=[N:6][CH:7]=1.CC1(C)C(C)(C)[O:17][B:16](B2OC(C)(C)C(C)(C)O2)[O:15]1.ClCCl.C([O-])(=O)C.[K+]>O1CCOCC1.CCOC(C)=O.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.C1C=CC(P(C2C=CC=CC=2)[C-]2C=CC=C2)=CC=1.Cl[Pd]Cl.[Fe+2].C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2]>[CH3:11][N:10]([CH3:12])[C:8]([C:5]1[N:6]=[CH:7][C:2]([B:16]([OH:17])[OH:15])=[CH:3][CH:4]=1)=[O:9]Participants
9
Reactant 4
Product 1
Reagents, catalysts & solvents 4
Conditions
- Temperature
- 120 °C
Procedure
A mixture of 5-bromo-N,N-dimethylpyridine-2-carboxamide (23 g, 98 mmol), 4,4,5,5,4′,4′,5′,5′-octamethyl-[2,2]bi[[1,3,2]dioxaborolanyl] (27 g, 110 mmol), [1,1′-bis(diphenylphosphino)ferrocene]dichloropalladium(II), complex with dichloromethane (1:1) (4.8 g, 5.9 mmol), 1,1′-bis(diphenylphosphino)ferrocene (3.3 g, 5.9 mmol), and potassium acetate (30 g, 300 mmol) in 1,4-dioxane (600 mL) was heated at 120° C. for 16 h. The mixture was cooled to rt and diluted with EtOAc. The organic solution was washed with saturated ammonium chloride solution which was discarded and then with water (1 L). The water wash was evaporated to give the desired compound (10 g, 50%). LCMS calculated for C8H12BN2O3 (M+H)+: m/z=195.1. found: 195.1.
Workup
- temperatureThe mixture was cooled to rt
- washThe organic solution was washed with saturated ammonium chloride solution which
- washThe water wash
- customwas evaporated
Sources & evidence
- ORD record
- ord-f6130e4ef57c4dc38ac59a44c666a420
- Source dataset
- uspto-grants-2015_08
- Patent number
- US09096600B2
Reaction notes
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