Sodium Acetate → HCID 50942140, compound

HRID 1919623Notes

Reaction equation

HRID 1919623 reaction equation
C([O-])(=O)C.[Na+].Br[C:7]1[CH:8]=[N:9][CH:10]=[CH:11][C:12]=1[C:13]([O:15]CC)=O.Cl.[NH2:19][C:20]1[CH:25]=[C:24]([C:26]#[N:27])[CH:23]=[CH:22][C:21]=1B(O)O>[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].O>[O:15]=[C:13]1[C:12]2[C:7](=[CH:8][N:9]=[CH:10][CH:11]=2)[C:21]2[CH:22]=[CH:23][C:24]([C:26]#[N:27])=[CH:25][C:20]=2[NH:19]1

Participants

6

Reactant 3

HCID 517045Sodium AcetateHCID 15141565Ethyl 3-bromoisonicotinateHCID 441187662-Amino-4-cyanobenzeneboronic acid hydrochloride

Product 1

HCID 50942140HCID 50942140, compoundYield 78.4%

Reagents, catalysts & solvents 2

HCID 178418228Bis(cyclopenta-1,4-dien-1-yl(diphenyl)phosphane);dichloropalladium;iron(2+)CatalystHCID 962WaterSolvent

Conditions

Temperature
120 °C

Procedure

Sodium acetate (410 mg, 5 mmol) and 1,1′-bis(diphenylphosphino)ferrocene palladium (II) chloride (complexed with dichloromethane) (36 mg, 0.05 mmol) were added to a mixture of ethyl 3-bromo-4-pyridine carboxylate (230 mg, 1.0 mmol) and 2-amino-4-cyanophenylboronic acid hydrochloric acid salt (179 mg, 0.9 mmol). The mixture was connected to an exit bubbler and heated to 120° C. for 18 hours at which time LCMS analysis indicated that the reaction was done based on the disappearance of starting material. After cooling to room temperature, water was added and the dark solids were filtered and washed with dichloromethane to give 5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-8-carbonitrile (156 mg) as a gray solid which was sufficiently pure enough for subsequent chemical transformations. LCMS (ESI) 222.4 (M+1)+. 1HNMR (400 MHz, DMSO-d6) 12.2 (1H, s), 9.96 (1H, s), 8.90 (1H, d, 5.1 Hz), 8.77 (1H, d, 8.2 Hz), 8.13 (1H, d, 5.1 Hz), 7.73 (1H, dd 8.2, 1.6 Hz), 7.70 (1H, d, 1.6 Hz).

Workup

  1. temperatureAfter cooling to room temperature
  2. filtrationthe dark solids were filtered
  3. washwashed with dichloromethane

Sources & evidence

ORD record
ord-fb52f04f2d6b4032958b14e8e1ba396e
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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