Dimethyl Ether → Benzo[c][1,5]naphthyridine

HRID 1715674Notes

Reaction equation

HRID 1715674 reaction equation
[NH2:1][C:2]1[C:3](Cl)=[N:4][CH:5]=[CH:6][CH:7]=1.COC.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C(=O)([O-])[O-].[Na+].[Na+].[CH:37]([C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1B(O)O)=O>C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:1]1[CH:2]=[CH:7][CH:6]=[C:5]2[C:37]=1[C:39]1[CH:44]=[CH:43][CH:42]=[CH:41][C:40]=1[CH:3]=[N:4]2

Participants

7

Reactant 5

HCID 8254Dimethyl EtherHCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 805282-Chloro-3-pyridylamineHCID 2921892-Formylphenylboronic acid

Product 1

HCID 12342817Benzo[c][1,5]naphthyridineYield 51%

Reagents, catalysts & solvents 1

HCID 167845palladium(II) acetateCatalyst

Procedure

2.3 g 3-amino-2-chloropyridine (20 mmol) was dissolved by 45 mL dimethyl ether (DME) in a round-bottomed flask. 0.24 g palladium acetate (Pd(OAc)2), 0.567 g triphenylphosphine (PPh3), and 27 mL sodium carbonate (Na2CO3) solution were mixed in another flask. After the two flasks were mixed and stirred until a white solid was precipitated, 3.5 g 2-formyl phenyl boronic acid (23.3 mmol) was added and stirred for 24 hr under nitrogen. After extraction by ethyl acetate, drying, concentration, and purification by silicon-gel column, 1.82 g yellow solid was obtained, with a yield of 51%.

Workup

  1. additionAfter the two flasks were mixed
  2. customwas precipitated
  3. stirringstirred for 24 hr under nitrogen
  4. extractionAfter extraction by ethyl acetate
  5. customdrying
  6. concentrationconcentration, and purification by silicon-gel column

Sources & evidence

ORD record
ord-b0adc973f6a24c4ebf269b10529a1739
Source dataset
uspto-grants-2010_09
Patent number
US07799918B2

Reaction notes

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