Water → 5-Fluoro-6-isopropenyl-pyridin-2-ylamine
Reaction equation
Br[C:2]1[N:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[F:9].[CH3:10][C:11]1(C)[C:15](C)(C)OB(C(C)=C)O1.P([O-])([O-])([O-])=O.[K+].[K+].[K+].O>CC(N(C)C)=O.CCOC(C)=O.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Pd]>[F:9][C:3]1[CH:4]=[CH:5][C:6]([NH2:8])=[N:7][C:2]=1[C:11]([CH3:15])=[CH2:10]Participants
Reactant 4
Product 1
Reagents, catalysts & solvents 3
Conditions
- Temperature
- 150 °C
Procedure
To a solution 6-bromo-5-fluoro-pyridin-2-ylamine (850 mg, 4.45 mmol) in dimethylacetamide (13.5 mL) was added 4,4,5,5-tetramethyl-2-(prop-1-en-2-yl)-1,3,2-dioxaborolane (1.09 mL, 5.79 mmol), palladium tetrakis(triphenylphosphine) (514 mg, 445 μmol) and tribasic potassium phosphate (1.89 g, 8.9 mmol) in water (4 mL, 223 mmol). The mixture was sealed in a microwave vial and heated at 150° C. in a microwave for 15 min. Upon cooling, the mixture was diluted with EtOAc, washed with water and brine, concentrated on to silica gel, and chromatographed (20% to 100% EtOAc in hexanes) to give 5-fluoro-6-isopropenyl-pyridin-2-ylamine contaminated with catalyst-derived impurities (−800 mg) that was used directly in the next step without further purification.
Workup
- customThe mixture was sealed in a microwave vial
- temperatureUpon cooling
- washwashed with water and brine
- concentrationconcentrated on to silica gel
- customchromatographed (20% to 100% EtOAc in hexanes)
Sources & evidence
- ORD record
- ord-5226b20ad52545c5b9649dab7bb6b98b
- Source dataset
- uspto-grants-2014_12
- Patent number
- US08901124B2
Reaction notes
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