Methyl 3-amino-4-methylbenzoate → Methyl 3-[(1-chloro-9-fluorobenzo[c]-2,6-naphthyridin-5-yl)amino]-4-methylbenzoate

HRID 1802466Notes

Reaction equation

HRID 1802466 reaction equation
[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=1[N:6]=[C:7]2Cl.[NH2:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:22]([O:24][CH3:25])=[O:23].CC(C)([O-])C.[Na+]>C1COCC1>[Cl:1][C:2]1[N:11]=[CH:10][CH:9]=[C:8]2[C:3]=1[C:4]1[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=1[N:6]=[C:7]2[NH:18][C:19]1[CH:20]=[C:21]([CH:26]=[CH:27][C:28]=1[CH3:29])[C:22]([O:24][CH3:25])=[O:23]

Participants

5

Reactant 3

HCID 337778Methyl 3-amino-4-methylbenzoateHCID 23676156Sodium t-butoxideHCID 594361181,5-Dichloro-9-fluorobenzo[c]-2,6-naphthyridine

Product 1

HCID 59436117Methyl 3-[(1-chloro-9-fluorobenzo[c]-2,6-naphthyridin-5-yl)amino]-4-methylbenzoate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

To a solution of 1,5-dichloro-9-fluorobenzo[c]-2,6-naphthytidine (Example 1, Step 5) (500 mg, 1.87 mmol) and methyl 3-amino-4-methylbenzoate (340 mg, 2.06 mmol) in THF (9.3 mL) was added sodium tert-butoxide (396 mg, 4.12 mmol). The reaction stirred at room temperature for ten minutes and was then quenched by the addition of sat. aq. NaHCO3 solution. The mixture was extracted with EtOAc and the extracts were washed with brine, dried over MgSO4 and concentrated in vacuo. Purification by silica gel column chromatography (0-30% EtOAc/heptane) afforded the title compound.

Workup

  1. customwas then quenched by the addition of sat. aq. NaHCO3 solution
  2. extractionThe mixture was extracted with EtOAc
  3. washthe extracts were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customPurification by silica gel column chromatography (0-30% EtOAc/heptane)

Sources & evidence

ORD record
ord-13067376039147abb3299da62522dbba
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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