Phosphorus oxychloride → 3-Bromo-8-chloro-1,7-naphthyridine
Reaction equation
[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:6](=O)[NH:7][CH:8]=[CH:9][C:10]=2[CH:11]=1.CCN(C(C)C)C(C)C.O=P(Cl)(Cl)[Cl:24]>C1(C)C=CC=CC=1>[Br:1][C:2]1[CH:3]=[N:4][C:5]2[C:10]([CH:11]=1)=[CH:9][CH:8]=[N:7][C:6]=2[Cl:24]Participants
5
Reactant 3
Product 1
Reagents, catalysts & solvents 1
Conditions
- Temperature
- 130 °C
Procedure
3-Bromo-7H-[1,7]naphthyridin-8-one (1.5 g, 6.67 mmol) was suspended in toluene (20 ml). DIPEA (3.5 ml, 20 mmol) and POCl3 (1.8 ml, 20 mmol) were added and the reaction mixture was heated to 130° C. for 36 h. The reaction mixture was cooled to rt and partitioned between water (75 ml) and EtOAc (150 ml). The phases were separated and the aq phase was extracted twice with EtOAc (25 ml). The combined organic layer was washed with NaHCO3 solution and brine, treated with MgSO4 and filtered. The filtrated was concentrated to give the desired product as a beige solid (1.1 g, 4.52 mmol).
Workup
- temperatureThe reaction mixture was cooled to rt
- custompartitioned between water (75 ml) and EtOAc (150 ml)
- customThe phases were separated
- extractionthe aq phase was extracted twice with EtOAc (25 ml)
- washThe combined organic layer was washed with NaHCO3 solution and brine
- additiontreated with MgSO4
- filtrationfiltered
- concentrationThe filtrated was concentrated
Sources & evidence
- ORD record
- ord-4615effa9530440cba8a79c65226ee5a
- Source dataset
- uspto-grants-2016_03
- Patent number
- US09284284B2
Reaction notes
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