Sodium Acetate → HCID 50942139, compound

HRID 533107Notes

Reaction equation

HRID 533107 reaction equation
Br[C:2]1[CH:12]=[N:11][CH:10]=[CH:9][C:3]=1[C:4]([O:6]CC)=O.[NH2:13][C:14]1[CH:19]=[C:18]([C:20]([O:22][CH3:23])=[O:21])[CH:17]=[CH:16][C:15]=1B(O)O.C([O-])(=O)C.[Na+]>[Pd](Cl)Cl.C1(P(C2C=CC=CC=2)[C-]2C=CC=C2)C=CC=CC=1.[C-]1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=C1.[Fe+2].CN(C)C=O>[O:6]=[C:4]1[C:3]2[C:2](=[CH:12][N:11]=[CH:10][CH:9]=2)[C:15]2[CH:16]=[CH:17][C:18]([C:20]([O:22][CH3:23])=[O:21])=[CH:19][C:14]=2[NH:13]1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 2737801(2-Amino-4-(methoxycarbonyl)phenyl)boronic acidHCID 15141565Ethyl 3-bromoisonicotinate

Product 1

HCID 50942139HCID 50942139, compoundYield 55.7%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
125 °C

Procedure

Ethyl 3-bromoisonicotinate (1.15 g, 5.0 mmol), 2-amino-4-(methoxycarbonyl)phenylboronic acid (1.04 g, 4.5 mmol), sodium acetate (1.64 g, 20 mmol), 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride (complexed with dichloromethane), (182 mg, 0.25 mmol) and dimethylformamide (7.5 mL) were combined in a flask. The flask was evacuated and filled with nitrogen twice and heated to 125° C. with stirring for 12 hours or until LCMS indicated the absence of any starting material. The mixture was cooled to room temperature and water (100 mL) was added to form a brown precipitate. The precipitate was filtered to yield 637 mg of methyl 5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-8-carboxylate. LCMS (ESI) 255.4 (M+1)+.

Workup

  1. customThe flask was evacuated
  2. additionfilled with nitrogen twice
  3. temperatureThe mixture was cooled to room temperature
  4. additionwater (100 mL) was added
  5. customto form a brown precipitate
  6. filtrationThe precipitate was filtered

Sources & evidence

ORD record
ord-b4471b2d5ffa48459d939217875144df
Source dataset
uspto-grants-2014_10
Patent number
US08853235B2

Reaction notes

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