Dimethyl malonate → HCID 66729193, compound

HRID 1098595Notes

Reaction equation

HRID 1098595 reaction equation
Cl[C:2]1[C:7]([N+:8]([O-:10])=[O:9])=[CH:6][C:5]([C:11]([F:14])([F:13])[F:12])=[CH:4][N:3]=1.[C:15]([O:22][CH3:23])(=[O:21])[CH2:16][C:17]([O:19][CH3:20])=[O:18].[H-].[Na+]>C1COCC1.CCOC(C)=O>[N+:8]([C:7]1[C:2]([CH:16]([C:15]([O:22][CH3:23])=[O:21])[C:17]([O:19][CH3:20])=[O:18])=[N:3][CH:4]=[C:5]([C:11]([F:14])([F:13])[F:12])[CH:6]=1)([O-:10])=[O:9]

Participants

6

Reactant 3

HCID 7943Dimethyl malonateHCID 24758Sodium hydrideHCID 47369502-Chloro-3-nitro-5-(trifluoromethyl)pyridine

Product 1

HCID 66729193HCID 66729193, compoundYield 56.2%

Reagents, catalysts & solvents 2

HCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of 2-chloro-3-nitro-5-(trifluoromethyl)pyridine from Example B16 (400 mg, 1.766 mmol) in THF (5 mL) was treated sequentially with dimethyl malonate (250 μl, 2.187 mmol) and sodium hydride (60%, 85 mg, 2.119 mmol). The resultant mixture was stirred at RT overnight. The mixture was diluted with EtOAc and washed with 0.1 M aq HCl, water, and brine, dried (MgSO4), concentrated in vacuo and purified by silica gel chromatography to provide dimethyl 2-(3-nitro-5-(trifluoromethyl)pyridin-2-yl)malonate (320 mg, 56% yield) of sufficient purity for the next step. MS (ESI) m/z: 323.0 (M+H+).

Workup

  1. washwashed with 0.1 M aq HCl, water, and brine
  2. dry with materialdried (MgSO4)
  3. concentrationconcentrated in vacuo
  4. custompurified by silica gel chromatography

Sources & evidence

ORD record
ord-f7f6b82b759c4932bffea6e943084414
Source dataset
uspto-grants-2012_03
Patent number
US08143293B2

Reaction notes

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