1-Methylindole → HCID 43161954, compound

HRID 1481688Notes

Reaction equation

HRID 1481688 reaction equation
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[CH:4]=[CH:3]1.CN(C)[C:13](=[O:17])[CH2:14][CH2:15][CH3:16].O=P(Cl)(Cl)Cl>C(Cl)(Cl)Cl>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][CH:7]=[CH:8][CH:9]=2)[C:4]([C:13](=[O:17])[CH2:14][CH2:15][CH3:16])=[CH:3]1

Participants

5

Reactant 3

HCID 117811-MethylindoleHCID 12973Butanamide, N,N-dimethyl-HCID 24813Phosphorus oxychloride

Product 1

HCID 43161954HCID 43161954, compoundYield 72%

Reagents, catalysts & solvents 1

HCID 6212ChloroformSolvent

Procedure

To a solution of 1-methyl-1H-indole (5.9 g, 45.0 mmol) in CHCl3 (150 mL) was added N,N-dimethylbutyramide (5.8 g, 50.4 mmol, 1.1 eq) followed by POCl3 (5.0 mL, 53.5 mmol, 1.2 eq) at 0° C. Then mixture was heated to reflux and stirred for 2 h. The reaction was quenched with saturated aqueous NaHCO3 then stirred for 30 min at room temperature. The mixture was extracted by CH2Cl2 (3×40 mL) and combined organic layers were dried over Na2SO4. The crude product was purified by flash column chromatography (0-50% EtOAc in hexanes) to afford 1-(1-methyl-1H-indol-3-yl)butan-1-one (6.53 g, 32.4 mmol, 72%).

Workup

  1. temperatureThen mixture was heated
  2. temperatureto reflux
  3. customThe reaction was quenched with saturated aqueous NaHCO3
  4. stirringthen stirred for 30 min at room temperature
  5. extractionThe mixture was extracted by CH2Cl2 (3×40 mL)
  6. dry with materialwere dried over Na2SO4
  7. customThe crude product was purified by flash column chromatography (0-50% EtOAc in hexanes)

Sources & evidence

ORD record
ord-8ae5af0590bc4e35ac18102c1ed72922
Source dataset
uspto-grants-2016_08
Patent number
US09409905B2

Reaction notes

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