Sodium Bicarbonate → HCID 86654527, compound

HRID 1189544Notes

Reaction equation

HRID 1189544 reaction equation
Cl.[NH2:2][CH2:3][C:4]([O:6][CH2:7][C:8]1[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=1)=[O:5].[Cl:14][C:15]1[CH:20]=[C:19]([C:21](=O)[CH2:22][CH2:23][C:24](=O)[CH3:25])[CH:18]=[CH:17][N:16]=1.C(=O)(O)[O-].[Na+]>ClCCl>[Cl:14][C:15]1[CH:20]=[C:19]([C:21]2[N:2]([CH2:3][C:4]([O:6][CH2:7][C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)=[O:5])[C:24]([CH3:25])=[CH:23][CH:22]=2)[CH:18]=[CH:17][N:16]=1

Participants

5

Reactant 3

HCID 516892Sodium BicarbonateHCID 11701227Benzyl 2-aminoacetate hydrochlorideHCID 247237241-(2-Chloropyridin-4-yl)pentane-1,4-dione

Product 1

HCID 86654527HCID 86654527, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
65 °C

Procedure

A slurry of benzyl 2-aminoacetate hydrochloride (922 mg, 4.57 mmol), 1-(2-chloropyridin-4-yl)pentane-1,4-dione (968 mg, 4.57 mmol), and solid sodium bicarbonate (961 mg, 11.4 mmol) in dichloromethane (15.2 mL) was heated to 45° C. for 14 hours. A significant amount of starting material was observed after 14 hours by LC/MS, so the reaction was heated to 65° C. The reaction was allowed to stir (with occasional monitoring by LCMS) at this temperature for 11 days. The reaction was then allowed to cool down to room temperature and poured onto water and extracted with dichloromethane (3×50 mL), dried (sodium sulfate), filtered, and concentrated to a dark orange residue. Purification was achieved by column chromatography (Luknova 80 g, 20 mL/min) using 5 to 45% ethyl acetate in hexanes over 60 minutes. The product, benzyl 2-(2-(2-chloropyridin-4-yl)-5-methyl-1H-pyrrol-1-yl)acetate was isolated as a light orange oil (890 mg, 2.61 mmol, 57% yield). 1H NMR (400 MHz, CDCl3): δ (ppm) 8.23 (d, 1H), 7.36-7.40 (m, 5H), 7.21 (m, 1H), 7.02 (dd, 1H), 6.37 (d, 1H), 6.07 (d, 1H), 5.25 (s, 2H), 4.64 (s, 2H), 2.22 (s, 3H).

Workup

  1. temperatureto cool down to room temperature
  2. additionpoured onto water
  3. extractionextracted with dichloromethane (3×50 mL)
  4. dry with materialdried (sodium sulfate)
  5. filtrationfiltered
  6. concentrationconcentrated to a dark orange residue
  7. customPurification
  8. customover 60 minutes

Sources & evidence

ORD record
ord-3c0f9fc41f8949719bddcbb1bd301cee
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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