HCID 86640304, compound → HCID 67005515, compound

HRID 563383Notes

Reaction equation

HRID 563383 reaction equation
[CH:1]([C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[CH:7]=[CH:6]2)=[O:2].[C:17]1([Mg]Br)[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1>C1COCC1>[OH:2][CH:1]([C:17]1[CH:22]=[CH:21][CH:20]=[CH:19][CH:18]=1)[C:3]1[CH:4]=[C:5]2[C:9](=[CH:10][CH:11]=1)[N:8]([C:12]([N:14]([CH3:16])[CH3:15])=[O:13])[CH:7]=[CH:6]2

Participants

4

Reactant 2

HCID 86640304HCID 86640304, compoundHCID 178418255HCID 178418255, compound

Product 1

HCID 67005515HCID 67005515, compoundYield 103.4%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent

Conditions

Temperature
-78 °C

Procedure

To a stirred solution of 5-formyl-N,N-dimethyl-1H-indole-1-carboxamide (0.63 g, 2.9 mmol) in anhydrous THF (5 mL) was added phenyl magnesium bromide solution (3 M in diethyl ether, 1.1 mL, 3.3 mmol) at −78° C. under argon. The reaction mixture was stirred at −78° C. for 1 hr, at rt for 1 hr and quenched by the slow addition of saturated aq ammonium chloride aqueous solution (10 mL) Water (10 mL) was added, the reaction mixture was extracted with ethyl acetate (20 mL) dried (Na2SO4), filtered through a pad of silica gel, and concentrated to give 5-(hydroxy(phenyl)methyl)-N,N-dimethyl-1H-indole-1-carboxamide (0.9 g, 3 mmol, 100% yield) as a syrup, the NMR spectrum of which was consistent with the desired structure.

Workup

  1. customquenched by the slow addition of saturated aq ammonium chloride aqueous solution (10 mL) Water (10 mL)
  2. additionwas added
  3. extractionthe reaction mixture was extracted with ethyl acetate (20 mL)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered through a pad of silica gel
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-97a4e9a45650469aa40d204054583475
Source dataset
uspto-grants-2011_11
Patent number
US08067447B2

Reaction notes

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