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

HRID 606926Notes

Reaction equation

HRID 606926 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)C.O1CCCC1.C(OCC)(=O)C>[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

6

Reactant 2

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

Product 1

HCID 67047758HCID 67047758, compoundYield 85.5%

Reagents, catalysts & solvents 3

HCID 3283Diethyl EtherSolventHCID 8028TetrahydrofuranSolventHCID 8857Ethyl AcetateSolvent

Procedure

Add a 3.0 M solution of methylmagnesium bromide (1.25 mL, 3.8 mmol) in diethyl ether dropwise to a cooled solution of N-methoxy-N-methyl-5-phenylethynyl -nicotinamide, (prepared as described in PREPARATION 2), (1.00 g, 3.7 mmol) in tetrahydrofuran (8.0 mL) at 0° C. Warm to room temperature, stir overnight and dilute with ethyl acetate. Wash with an aqueous saturated solution of ammonium chloride, dry (magnesium chloride), filter and concentrate. Purify the residue by silica gel chromatography, eluting with 10:90 to 30:70 tetrahydrofuran:hexanes, to give the title compound as a white solid (0.70 g, 84%).

Workup

  1. washWash with an aqueous saturated solution of ammonium chloride
  2. dry with materialdry (magnesium chloride)
  3. filtrationfilter
  4. concentrationconcentrate
  5. customPurify the residue by silica gel chromatography
  6. washeluting with 10:90 to 30:70 tetrahydrofuran

Sources & evidence

ORD record
ord-d1a93ca48a344f028f3b22e1cfdd130a
Source dataset
uspto-grants-2011_03
Patent number
US07915424B2

Reaction notes

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