Dimethylformamide → HCID 21931746, compound

HRID 1244041Notes

Reaction equation

HRID 1244041 reaction equation
[CH3:1][O:2][C:3]1[N:8]=[C:7]2[CH2:9][C:10](=O)NC2=[CH:5][CH:4]=1.[CH3:13]I.[CH3:15][N:16]([CH:18]=[O:19])[CH3:17]>>[CH3:1][O:2][C:3]1[N:8]=[C:7]2[C:9]([CH3:10])([CH3:13])[C:18](=[O:19])[N:16]([CH3:17])[C:15]2=[CH:5][CH:4]=1

Participants

4

Reactant 3

HCID 6228DimethylformamideHCID 6328Methyl iodideHCID 107733215-Methoxy-4-aza-2-oxindole

Product 1

HCID 21931746HCID 21931746, compound

Conditions

Temperature
0 °C

Procedure

A solution of 0.2 g (1.22 mmol) 5-methoxy-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one (J. Het. Chem. 1996, 33, 287–93) was dissolved in 10 ml of DMF and cooled to 0° C. under a nitrogen atmosphere in a flame dried round bottom flask. To this solution was added 4.02 ml (4.02 mmol) of a 1M solution of potassium t-butoxide in THF and the solution was stirred for 10 minutes. To this solution was added dropwise 0.3 ml (4.88 mmol) of MeI, and the reaction was stirred for 15 minutes at 0° C. The reaction was quenched with water and extracted with ethyl acetate. The ethyl acetate extracts were dried (Na2SO4) and evaporated. The residue was chromatographed on 6 g of silica using 3:1 hexanes/ethyl acetate as the elutant. Appropriate fractions were combined and evaporated to yield 0.14 g of 5-methoxy-1,3,3-trimethyl-1,3-dihydro-pyrrolo[3,2-b]pyridin-2-one. 1H NMR (CDCl3) δ 7.02 (d, 1H), 6.58 (d, 1H), 3.90 (s, 3H), 3.18 (s, 3H), 1.38 (s, 6H). Mass spectrum: m/e=207 (P+1).

Workup

  1. customdried round bottom flask
  2. additionTo this solution was added 4.02 ml (4.02 mmol) of a 1M solution of potassium t-butoxide in THF
  3. stirringthe reaction was stirred for 15 minutes at 0° C
  4. customThe reaction was quenched with water
  5. extractionextracted with ethyl acetate
  6. dry with materialThe ethyl acetate extracts were dried (Na2SO4)
  7. customevaporated
  8. customThe residue was chromatographed on 6 g of silica using 3:1 hexanes/ethyl acetate as the elutant
  9. customevaporated

Sources & evidence

ORD record
ord-aec85dda45e242fe9ed1f9491cd08475
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

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