Sodium bis(trimethylsilyl)amide → Methyl 5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-7-carboxylate

HRID 1919682Notes

Reaction equation

HRID 1919682 reaction equation
N[C:2]1[C:11]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][C:17]=2[C:18](=[O:26])[N:19](C(C)C)C(C)C)=[CH:10][CH:9]=[CH:8][C:3]=1[C:4]([O:6][CH3:7])=[O:5].C[Si]([N-][Si](C)(C)C)(C)C.[Na+]>C1COCC1>[O:26]=[C:18]1[C:17]2[C:12](=[CH:13][N:14]=[CH:15][CH:16]=2)[C:11]2=[CH:10][CH:9]=[CH:8][C:3]([C:4]([O:6][CH3:7])=[O:5])=[C:2]2[NH:19]1

Participants

4

Reactant 2

HCID 2724254Sodium bis(trimethylsilyl)amideHCID 50941398Methyl 2-amino-3-(4-(diisopropylcarbamoyl)pyridin-3-yl)benzoate

Product 1

HCID 50941290Methyl 5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-7-carboxylate

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Procedure

Methyl 2-amino-3-(4-(diisopropylcarbamoyl)pyridin-3-yl)benzoate (1.0 eq, 244 mg, 0.686 mmol) was dissolved under nitrogen atmosphere in anhydrous THF (1.5 ml). A NaHMDS solution (1.0 M in THF, 2.0 eq, 1.4 ml, 1.4 mmol) was added dropwise through syringe. The resulting suspension was stirred at room temperature for 1 hour. The reaction was quenched by addition of a saturated aqueous solution of ammonium chloride. The solid that formed was filtered and dried. After trituration in methanol and filtration, methyl 5-oxo-5,6-dihydrobenzo[c][2,6]naphthyridine-7-carboxylate was isolated as a grey fluffy solid (93 mg, 53% yield). LCMS (ES): >95% pure, m/z 255 [M+1]+.

Workup

  1. customThe reaction was quenched by addition of a saturated aqueous solution of ammonium chloride
  2. customThe solid that formed
  3. filtrationwas filtered
  4. customdried
  5. filtrationAfter trituration in methanol and filtration

Sources & evidence

ORD record
ord-56da8a07ad5c4c5386c1faf80d49db8d
Source dataset
uspto-grants-2012_05
Patent number
US08168651B2

Reaction notes

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