Potassium Sodium Tartrate → HCID 86622467, compound

HRID 606800

Reaction equation

HRID 606800 reaction equation
C[Al](C)C.C(O[C:8](=[O:24])[C:9]1[CH:14]=[C:13]([C:15]#[C:16][C:17]2[CH:22]=[CH:21][CH:20]=[C:19]([F:23])[CH:18]=2)[CH:12]=[N:11][CH:10]=1)C.[CH3:25][NH:26][O:27][CH3:28].[C@H](O)(C([O-])=O)[C@@H](O)C([O-])=O.[Na+].[K+]>C1(C)C=CC=CC=1.C(OCC)(=O)C>[F:23][C:19]1[CH:18]=[C:17]([C:16]#[C:15][C:13]2[CH:12]=[N:11][CH:10]=[C:9]([CH:14]=2)[C:8]([N:26]([O:27][CH3:28])[CH3:25])=[O:24])[CH:22]=[CH:21][CH:20]=1

Participants

7

Reactant 4

HCID 9357Potassium Sodium TartrateHCID 14232N,O-DimethylhydroxylamineHCID 16682925TrimethylaluminumHCID 670477625-(3-Fluorophenylethynyl)-nicotinic acid ethyl ester

Product 1

HCID 86622467HCID 86622467, compoundYield 33.2%

Reagents, catalysts & solvents 2

HCID 1140TolueneSolvent2×HCID 8857Ethyl AcetateSolvent

Procedure

Sequentially add a 2 M solution of trimethylaluminum in toluene (0.64 g, 8.91 mmol) and 5-(3-fluorophenylethynyl)-nicotinic acid ethyl ester (0.24 g, 0.89 mmol), (prepared essentially as described in PREPARATION 17), to a solution of N,O-dimethylhydroxylamine (0.435 g, 4.46 mmol) in anhydrous toluene (4.0 mL) at 0° C. After 30 min, warm to room temperature and stir overnight. Dilute the reaction with ethyl acetate and an aqueous saturated solution of Rochelle salt (potassium sodium tartrate) and stir vigorously for 1 h. Separate the organic layer; dry (magnesium sulfate), filter and concentrate. Purify the resulting residue by silica gel chromatography, eluting with a linear gradient of 100:0 to 60:40 tetrahydrofuran:hexanes, to give the title compound as a pale yellow oil (0.084 g, 33%).

Workup

  1. custom(prepared essentially
  2. additionDilute
  3. customSeparate the organic layer
  4. dry with materialdry (magnesium sulfate)
  5. filtrationfilter
  6. concentrationconcentrate
  7. customPurify the resulting residue by silica gel chromatography
  8. washeluting with a linear gradient of 100:0 to 60:40 tetrahydrofuran

Sources & evidence

ORD record
ord-587fed56830847d1b4748c7a75299f09
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Linked notes

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