Methanol → 1-Ethoxy-9-fluorobenzo[c]-2,6-naphthyridin-5(6H)-one

HRID 1802452Notes

Reaction equation

HRID 1802452 reaction equation
N[C:2]1[CH:7]=[CH:6][C:5]([F:8])=[CH:4][C:3]=1[C:9]1[C:23]([O:24][CH2:25][CH3:26])=[N:22][CH:21]=[CH:20][C:10]=1[C:11]([N:13](C(C)C)C(C)C)=[O:12].C[Si](C)(C)N[Si](C)(C)C.[Na].CO>C1COCC1>[CH2:25]([O:24][C:23]1[N:22]=[CH:21][CH:20]=[C:10]2[C:9]=1[C:3]1[CH:4]=[C:5]([F:8])[CH:6]=[CH:7][C:2]=1[NH:13][C:11]2=[O:12])[CH3:26]

Participants

5

Reactant 3

HCID 887MethanolHCID 45051731Sodium hexamethyidisilazaneHCID 594360763-(2-Amino-5-fluorophenyl)-2-ethoxy-N,N-diisopropylisonicotinamide

Product 1

HCID 594361071-Ethoxy-9-fluorobenzo[c]-2,6-naphthyridin-5(6H)-one

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 3-(2-amino-5-fluorophenyl)-2-ethoxy-N,N-diisopropylisonicotinamide (170 mg, 0.473 mmol) in THF (3153 μl), was added sodium hexamethyldisilazane (946 μl, 0.946 mmol, 1.0 M in THF). The reaction mixture was stirred at room temperature for 30 min. Methanol was added and the mixture was concentrated under reduced pressure. The residue was then triturated with diethyl ether (25 mL) and stirred for 1 h. The mixture was filtered through a frit, and the filter cake was collected and dried to afford the title compound as a beige solid.

Workup

  1. concentrationthe mixture was concentrated under reduced pressure
  2. customThe residue was then triturated with diethyl ether (25 mL)
  3. stirringstirred for 1 h
  4. filtrationThe mixture was filtered through a frit
  5. customthe filter cake was collected
  6. customdried

Sources & evidence

ORD record
ord-bb7d883b9aa945e89e349759696498b4
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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