Potassium Carbonate → HCID 69736033, compound

HRID 497418Notes

Reaction equation

HRID 497418 reaction equation
P(Cl)(Cl)(Cl)=O.[CH2:6]([O:8][C:9]([C:11]1[C:15]([C:16]2[C:21]([NH:22][C:23](OCC3C=CC=CC=3)=O)=[CH:20][CH:19]=[C:18]([O:33][CH3:34])N=2)=[CH:14][NH:13][CH:12]=1)=[O:10])[CH3:7].[C:35](=O)(O)[O-].[Na+].C([O-])([O-])=O.[K+].[K+]>CN(C=O)C>[CH2:6]([O:8][C:9]([C:11]1[C:15]2[C:16]3[CH:35]=[C:18]([O:33][CH3:34])[CH:19]=[CH:20][C:21]=3[N:22]=[CH:23][C:14]=2[NH:13][CH:12]=1)=[O:10])[CH3:7]

Participants

6

Reactant 4

HCID 11430Potassium CarbonateHCID 24813Phosphorus oxychlorideHCID 516892Sodium BicarbonateHCID 69735828HCID 69735828, compound

Product 1

HCID 69736033HCID 69736033, compound

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent2×

Procedure

A 10 mL aliquot DMF is cooled to 5° C. To this is added 2.26 mL (0.024 mol) of phosphorous oxychloride. The mixture is warmed to room temperature, stirred for 15 minutes and cooked to 5° C. To this solution is added dropwise a solution 3.2 g (0.08 mol) of 4-(benzyloxycarbonylamino-6-methoxy-pyridin-2-yl)-1H-pyrrole-3-carboxylic acid ethyl ester dissolved in 15 mL of DMF. The reaction mixture is warmed to room temperature and stirred for 3 hours. The reaction mixture is carefully poured into 100 mL of saturated sodium bicarbonate. The pH is adjusted to 8 with solid K2CO3 and the mixture extracted with ethyl acetate. The organic extracts are dried (Na2SO4) and evaporated. The residue is chromatographed on 150 g of silica gel using ethyl acetate followed by 10/1 chloroform/methanol as the eluant. Appropriate fractions are combined to yield 1.46 grams of 8-methoxy-3H-pyrrolo[2,3-c]quinoline-1-carboxylic acid ethyl ester. 1H NMR (CDCl3) δ 9.10 (s, 1H), 8.35 (d, 1H), 8.10 (s, 1H, 7.2 (s, 1H), 7.05 (d, 1H), 4.4 (q, 2H), 4.10 (s, 3H), 1.40 (t, 3H). Mass spectrum: m/e=260 (p+1). TLC (ethyl acetate) Rf=0.3. Step 8:

Workup

  1. customcooked to 5° C
  2. temperatureThe reaction mixture is warmed to room temperature
  3. stirringstirred for 3 hours
  4. extractionthe mixture extracted with ethyl acetate
  5. dry with materialThe organic extracts are dried (Na2SO4)
  6. customevaporated
  7. customThe residue is chromatographed on 150 g of silica gel

Sources & evidence

ORD record
ord-2411b7f149b94d5da368664032fd06cd
Source dataset
uspto-grants-2005_09
Patent number
US06949562B2

Reaction notes

Loading…