Triphenylphosphine → HCID 86663080, compound
Reaction equation
P([O-])([O-])([O-])=O.[K+].[K+].[K+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[Cl:28][C:29]1[N:34]=[C:33]([NH2:35])[CH:32]=[CH:31][C:30]=1I.[CH3:37][O:38][C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1B(O)O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:28][C:29]1[N:34]=[C:33]([NH2:35])[C:32]([C:40]2[CH:41]=[CH:42][CH:43]=[CH:44][C:39]=2[O:38][CH3:37])=[CH:31][CH:30]=1Participants
6
Conditions
- Temperature
- 75 °C
Procedure
Potassium phosphate (12.72 g, 60 mmol), triphenyl phosphine (0.682 g, 2.40 mmol), 6-chloro-5-iodo-2-aminopyridine (6.1 g, 24 mmol), 2-methoxybenzeneboronic acid (5.10 g, 33.5 mmol) and palladium acetate (0.27 g, 1.20 mmol) were sequentially added to degassed acetonitrile (200 mL) and water (60 mL) under nitrogen. The reaction mixture was heated at 75° C. for overnight, then cooled to room temperature. The organic layer was separated and aqueous layer and was extracted with ethyl acetate. The combined organic layers were dried over sodium sulfate, concentrated and purified by silica column using hexanes and ethyl acetate as eluent furnishing 4.05 g of title compound.
Workup
- customto degassed acetonitrile (200 mL) and water (60 mL) under nitrogen
- temperaturecooled to room temperature
- customThe organic layer was separated
- extractionaqueous layer and was extracted with ethyl acetate
- dry with materialThe combined organic layers were dried over sodium sulfate
- concentrationconcentrated
- custompurified by silica column
Sources & evidence
- ORD record
- ord-afb4646395c1452f832fe7ea2fb73afd
- Source dataset
- uspto-grants-2016_06
- Patent number
- US09359549B2
Reaction notes
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