Sodium Carbonate → 3-(6-Amino-1,7-naphthyridin-8-yl)benzonitrile

HRID 2376626Notes

Reaction equation

C(=O)([O-])[O-].[Na+].[Na+].[NH2:7][C:8]1[CH:9]=[C:10]2[C:15](=[C:16](Br)[N:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[C:38]([C:40]1[CH:41]=[C:42](B(O)O)[CH:43]=[CH:44][CH:45]=1)#[N:39]>C1COCC1>[NH2:7][C:8]1[CH:9]=[C:10]2[C:15](=[C:16]([C:44]3[CH:43]=[CH:42][CH:41]=[C:40]([C:38]#[N:39])[CH:45]=3)[N:17]=1)[N:14]=[CH:13][CH:12]=[CH:11]2

Participants

Conditions

Temperature: 80 °C

Procedure

To a mixture of THF (80 ml) and 2N sodium carbonate (34 ml, aqueous) is added 6-amino-8-bromo-1,7-naphthyridine (4.007 g), triphenylphosphine (0.37 g) and 3-cyanophenyl-boronic acid (3.23 g). The mixture is degassed under argon three times and then bis(di-benzylidene-acetone)palladium (0) (0.4 g) is added and the mixture is degassed under argon three more times. The mixture is heated at 80° C. under argon for 16 hours then cooled and filtered. The mixture is diluted with ethyl acetate and washed with 2N sodium hydroxide then brine. After drying over sodium sulfate the organic layer is evaporated and suspended in ether. The solid precipitate thus obtained is the title compound, which is filtered off.

Workup

customThe mixture is degassed under argon three times
additionbis(di-benzylidene-acetone)palladium (0) (0.4 g) is added
customthe mixture is degassed under argon three more times
temperaturethen cooled
filtrationfiltered
additionThe mixture is diluted with ethyl acetate
washwashed with 2N sodium hydroxide
dry with materialAfter drying over sodium sulfate the organic layer
customis evaporated
customThe solid precipitate thus obtained

Sources & evidence

ORD record: ord-1f9798692d644766ae1f77ba5d3e54ab
Source dataset: uspto-grants-2008_12
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07468370B2

Reaction notes

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