Water → HCID 21931654, compound

HRID 1244046Notes

Reaction equation

HRID 1244046 reaction equation
Cl[C:2]1[N:7]=[C:6]2[N:8]([CH3:14])[C:9](=[O:13])[C:10]([CH3:12])([CH3:11])[C:5]2=[CH:4][CH:3]=1.[CH3:15][O-:16].[Na+].O>CN(C=O)C>[CH3:15][O:16][C:2]1[N:7]=[C:6]2[N:8]([CH3:14])[C:9](=[O:13])[C:10]([CH3:12])([CH3:11])[C:5]2=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 962WaterHCID 10942334Sodium MethoxideHCID 21931732HCID 21931732, compound

Product 1

HCID 21931654HCID 21931654, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
145 °C

Procedure

A mixture of 0.3 g (1.4 mmol) 6-chloro-1,3,3-trimethyl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one, 0.6 ml (2.8 mmol) of sodium methoxide (4.6M in methanol), and 1.2 mg of Cul in 6 ml of DMF was heated to 145° C. for 18 hours. The reaction mixture was cooled to room temperature and added to 25 ml of water. The mixture was extracted with ethyl acetate. The ethyl acetate extract were was washed with 25 ml of saturated sodium bisulfite, dried (Na2SO4) and evaporated. The residue was triturated twice with hot hexane, and the hexane decanted. The residue 6-methoxy-1,3,3-trimethyl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (0.25 g) was used without further purification. TLC: Rf=0.7 (5:1 hexane/ethyl acetate). 1H NMR (CDCl3) δ 7.35 (d, 1H), 6.38 (d, 1H), 3.92 (s, 3H), 3.22 (s, 3H), 1.33 (s, 3H). Mass spectrum: m/e=207.3 (p+1).

Workup

  1. temperatureThe reaction mixture was cooled to room temperature
  2. extractionThe mixture was extracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwere was washed with 25 ml of saturated sodium bisulfite
  5. dry with materialdried (Na2SO4)
  6. customevaporated
  7. customThe residue was triturated twice with hot hexane
  8. customthe hexane decanted
  9. customThe residue 6-methoxy-1,3,3-trimethyl-1,3-dihydro-pyrrolo[2,3-b]pyridin-2-one (0.25 g) was used without further purification

Sources & evidence

ORD record
ord-8bb521c319654927a0d7971541f82e12
Source dataset
uspto-grants-2006_10
Patent number
US07119207B2

Reaction notes

Loading…