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

HRID 917306Notes

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]>O1CCCC1>[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 tetrahydrofuran (THF) (80 ml) and 2 N sodium carbonate (34 ml, aqueous) is added 6-amino-8-bromo-1,7-naphthyridine (4.007 g), triphenylphosphine (0.37 g) and 3-cyanophenylboronic acid (323 g). The mixture is degassed under argon three times and then bis(dibenzylideneacetone)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 2 N 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. M.p. 182-184° C. HRMS [M+H]+ found=247.1.

Workup

customThe mixture is degassed under argon three times
additionbis(dibenzylideneacetone)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 2 N sodium hydroxide
dry with materialAfter drying over sodium sulfate the organic layer
customis evaporated
customThe solid precipitate thus obtained

Sources & evidence

ORD record: ord-07ae8c5be78942119c01e76e5317a1ee
Source dataset: uspto-grants-2007_09
DOI: 10.6084/m9.figshare.5104873.v1
Patent number: US07273875B2

Reaction notes

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