Ethyl Acetate → HCID 86305809, compound
Reaction equation
Br[C:2]1[CH:3]=[C:4]2[C:9](=[N:10][CH:11]=1)[N:8]([C:12]([NH2:14])=[O:13])[CH2:7][CH2:6][C:5]2([F:16])[F:15].CC1(C)C(C)(C)OB([C:25]2[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=2)O1.C([O-])([O-])=O.[K+].[K+].CCOC(C)=O>O1CCOCC1.O.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.CC(P(C(C)(C)C)C1C=CC(N(C)C)=CC=1)(C)C.Cl[Pd]Cl>[F:15][C:5]1([F:16])[C:4]2[C:9](=[N:10][CH:11]=[C:2]([C:25]3[CH:26]=[N:27][CH:28]=[CH:29][CH:30]=3)[CH:3]=2)[N:8]([C:12]([NH2:14])=[O:13])[CH2:7][CH2:6]1Participants
7
Reactant 4
Product 1
Reagents, catalysts & solvents 2
Conditions
- Temperature
- 100 °C
Procedure
A mixture of 6-bromo-4,4-difluoro-3,4-dihydro-2H [1,8]naphthyridine-1-carboxylic acid amide (89.6 mg, 0.31 mmol), 3-(4,4,5,5-tetramethyl-[1,3,2]dioxaborolan-2-yl)-pyridine (92.3 mg, 0.46 mmol), K2CO3 (105 mg, 0.77 mmol) and bis(di-tert-butyl(4-dimethylaminophenyl)phosphine)dichloropalladium (II) (21.8 mg, 0.03 mmol) in 1 mL dioxane/water (9:1) is heated at 100° C. for 2 hrs. 30 mL of EtOAc is added. The mixture is washed with 2×10 mL of NaHCO3 and 1×10 mL brine. The organic phase is dried with MgSO4, filtered and concentrated. The residue is applied to a silica preparative TLC plate and purified (10% MeOH/CH2Cl2) to give 39.9 mg of the titled product.
Workup
- washThe mixture is washed with 2×10 mL of NaHCO3 and 1×10 mL brine
- dry with materialThe organic phase is dried with MgSO4
- filtrationfiltered
- concentrationconcentrated
- custompurified (10% MeOH/CH2Cl2)
Sources & evidence
- ORD record
- ord-ca71927872e3427680ddda2f255566fa
- Source dataset
- uspto-grants-2015_11
- Patent number
- US09181272B2
Reaction notes
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