Sodium bis(trimethylsilyl)amide → N-(5-tert-Butyl-2-methylphenyl)-1-chloro-9-fluorobenzo[c]-2,6-naphthyridin-5-amine

HRID 1802458Notes

Reaction equation

HRID 1802458 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.[C:18]([C:22]1[CH:23]=[CH:24][C:25]([CH3:29])=[C:26]([CH:28]=1)[NH2:27])([CH3:21])([CH3:20])[CH3:19].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>CC(N(C)C)=O>[C:18]([C:22]1[CH:23]=[CH:24][C:25]([CH3:29])=[C:26]([NH:27][C:7]2[C:8]3[C:3](=[C:2]([Cl:1])[N:11]=[CH:10][CH:9]=3)[C:4]3[CH:16]=[C:15]([F:17])[CH:14]=[CH:13][C:5]=3[N:6]=2)[CH:28]=1)([CH3:21])([CH3:20])[CH3:19]

Participants

5

Reactant 3

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 130899795-tert-Butyl-2-methylanilineHCID 594361181,5-Dichloro-9-fluorobenzo[c]-2,6-naphthyridine

Product 1

HCID 59436103N-(5-tert-Butyl-2-methylphenyl)-1-chloro-9-fluorobenzo[c]-2,6-naphthyridin-5-amine

Reagents, catalysts & solvents 1

HCID 31374DimethylacetamideSolvent

Procedure

To a solution of 1,5-dichloro-9-fluorobenzo[c]-2,6-naphthyridin (Example 1, Step 5) (150 mg, 0.56 mmol) and 5-tert-butyl-2-methylaniline (101 mg, 0.62 mmol) in DMA (2.8 mL) was added NaHMDS (1 M in THF, 1.2 mL, 1.2 mmol) at 0° C. After stirring for 45 minutes, the reaction was quenched by the addition of sat. aq. NaHCO3. The reaction was then extracted with EtOAc and water. The organic extracts were dried over MgSO4 and concentrated in vacuo. Column chromatography on silica gel (100% hexane to 100% EtOAc) provided the title compound.

Workup

  1. customthe reaction was quenched by the addition of sat. aq. NaHCO3
  2. extractionThe reaction was then extracted with EtOAc and water
  3. dry with materialThe organic extracts were dried over MgSO4
  4. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-aa07f1c68b7943aaaca920a6691bb40b
Source dataset
uspto-grants-2013_01
Patent number
US08349865B2

Reaction notes

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