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Potassium bis(trimethylsilyl)amide → 6-[3-(4-Methoxy-3-methyl-benzoyl)-4-oxo-4H-[1,8]naphthyridin-1-ylmethyl]-pyridine-2-carbonitrile

HRID 227134
Notes
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Reaction equation

HRID 227134 reaction equation
[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[NH:11][CH:10]=2)=[O:8])=[CH:5][C:4]=1[CH3:22].C[Si]([N-][Si](C)(C)C)(C)C.[K+].Br[CH2:34][C:35]1[N:40]=[C:39]([C:41]#[N:42])[CH:38]=[CH:37][CH:36]=1>C1COCC1>[CH3:1][O:2][C:3]1[CH:21]=[CH:20][C:6]([C:7]([C:9]2[C:18](=[O:19])[C:17]3[C:12](=[N:13][CH:14]=[CH:15][CH:16]=3)[N:11]([CH2:34][C:35]3[N:40]=[C:39]([C:41]#[N:42])[CH:38]=[CH:37][CH:36]=3)[CH:10]=2)=[O:8])=[CH:5][C:4]=1[CH3:22]
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

5

Reactant 3

HCID 3251421Potassium bis(trimethylsilyl)amideHCID 272816606-(Bromomethyl)pyridine-2-carbonitrileHCID 577545283-(4-Methoxy-3-methyl-benzoyl)-1H-[1,8]naphthyridin-4-one

Product 1

HCID 577546756-[3-(4-Methoxy-3-methyl-benzoyl)-4-oxo-4H-[1,8]naphthyridin-1-ylmethyl]-pyridine-2-carbonitrileYield 21.5%

Reagents, catalysts & solvents 1

HCID 8028
Tetrahydrofuran
Solvent
2×

Procedure

Experimental conditions analogous to those described for Step 3 of Example 1, from 50 mg (0.17 mmol) of 3-(4-Methoxy-3-methyl-benzoyl)-1H-[1,8]naphthyridin-4-one in THF 2 ml, was added KHMDS in THF 0.4 ml (0.2 mmol ) slowly. The reaction mixture was stirred at room temperature for 60 min, followed by the addition of 40 mg (0.2 mmol) of 6-Bromomethyl-pyridine-2-carbonitrile. The mixture was heated to 60° C. for 60 min, then quenched with water and purified with HPLC to give the desired product (15 mg). LCMS (M+H)+: 411.1.

Workup

  1. temperatureThe mixture was heated to 60° C. for 60 min
  2. customquenched with water
  3. custompurified with HPLC

Sources & evidence

ORD record
ord-b0d55dee38384380b3fad59ce1bfb4ef
Source dataset
uspto-grants-2009_07
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US07557213B2

Reaction notes

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On this pageParticipantsProcedureWorkupSources & evidenceReaction notes