Potassium Carbonate → HCID 69736033, compound

HRID 481100Notes

Reaction equation

HRID 481100 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) δ9.10 (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.

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-41d940d6bc02497d80815b056f655472
Source dataset
uspto-grants-2003_11
Patent number
US06653471B2

Reaction notes

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