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

HRID 917306
Notes
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Reaction equation

HRID 917306 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
ParticipantsConditionsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 4

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 27343253-Cyanophenylboronic acidHCID 107043358-Bromo-1,7-naphthyridin-6-amine

Product 1

HCID 107055713-(6-Amino-1,7-naphthyridin-8-yl)benzonitrile

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent

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

  1. customThe mixture is degassed under argon three times
  2. additionbis(dibenzylideneacetone)palladium (0) (0.4 g) is added
  3. customthe mixture is degassed under argon three more times
  4. temperaturethen cooled
  5. filtrationfiltered
  6. additionThe mixture is diluted with ethyl acetate
  7. washwashed with 2 N sodium hydroxide
  8. dry with materialAfter drying over sodium sulfate the organic layer
  9. customis evaporated
  10. 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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On this pageParticipantsConditionsProcedureWorkupSources & evidenceReaction notes