N-Methoxy-N-methyl-5-phenylethynylnicotinamide → HCID 67047758, compound

HRID 606867Notes

Reaction equation

HRID 606867 reaction equation
[CH3:1][Mg]Br.CON(C)[C:7](=[O:22])[C:8]1[CH:13]=[C:12]([C:14]#[C:15][C:16]2[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=2)[CH:11]=[N:10][CH:9]=1>C(OCC)(=O)C.[Cl-].[NH4+]>[C:16]1([C:15]#[C:14][C:12]2[CH:13]=[C:8]([C:7](=[O:22])[CH3:1])[CH:9]=[N:10][CH:11]=2)[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1

Participants

5

Reactant 2

HCID 86076555N-Methoxy-N-methyl-5-phenylethynylnicotinamideHCID 178418573HCID 178418573, compound

Product 1

HCID 67047758HCID 67047758, compoundYield 84%

Reagents, catalysts & solvents 2

HCID 8857Ethyl AcetateSolventHCID 25517Ammonium ChlorideSolvent

Procedure

Add methylmagnesium bromide (1.25 mL, 3.7 mmol) dropwise at 0° C. to a solution of N-methoxy-N-methyl-5-phenylethynylnicotinamide, (prepared essentially as described in PREPARATION 2), (1.0 g, 3.76 mmol). Allow the mixture to warn to room temperature overnight. Dilute with ethyl acetate and saturated ammonium chloride, dry (magnesium sulfate), concentrate and purify (silica gel chromatography, eluting with 10:90 to 30:70 tetrahydrofuran:hexanes) to give title compound as a white solid (0.70 g, 84%).

Workup

  1. custom(prepared essentially
  2. customas described in PREPARATION 2), (1.0 g, 3.76 mmol)
  3. dry with materialdry (magnesium sulfate)
  4. concentrationconcentrate
  5. custompurify
  6. wash(silica gel chromatography, eluting with 10:90 to 30:70 tetrahydrofuran:hexanes)

Sources & evidence

ORD record
ord-61449d423ab94c7cbd02057cad914deb
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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