Ethyl (2,5-dimethyl-1H-pyrrol-1-yl)acetate → HCID 53246737, compound

HRID 1189585Notes

Reaction equation

HRID 1189585 reaction equation
[CH3:1][C:2]1[N:3]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:4]([CH3:7])=[CH:5][CH:6]=1.[Cl-].C([Al+]CC)C.[O:20]1[CH2:25][CH2:24][N:23]([S:26]([C:29]2[CH:37]=[CH:36][CH:35]=[CH:34][C:30]=2[C:31](Cl)=[O:32])(=[O:28])=[O:27])[CH2:22][CH2:21]1>ClCCl>[CH3:7][C:4]1[N:3]([CH2:8][C:9]([O:11][CH2:12][CH3:13])=[O:10])[C:2]([CH3:1])=[CH:6][C:5]=1[C:31](=[O:32])[C:30]1[CH:34]=[CH:35][CH:36]=[CH:37][C:29]=1[S:26]([N:23]1[CH2:22][CH2:21][O:20][CH2:25][CH2:24]1)(=[O:28])=[O:27]

Participants

5

Reactant 3

HCID 12894114Ethyl (2,5-dimethyl-1H-pyrrol-1-yl)acetateHCID 13140214HCID 13140214, compoundHCID 16686102Diethyl aluminum chloride

Product 1

HCID 53246737HCID 53246737, compoundYield 30.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. solution of ethyl 2-(2,5-dimethyl-1H-pyrrol-1-yl)acetate (0.2 g, 1.10 mmol) in dichloromethane (8.0 mL) was added diethylaluminum chloride (1.66 mL, 1.66 mmol). The reaction was stirred at 0° C. for 15 minutes, after which a solution of 2-(morpholinosulfonyl)benzoyl chloride (0.384 g, 1.32 mmol) was added. The reaction was stirred for 30 minutes at 0° C., then allowed to warm to room temperature, and stirred for 3 hours at this temp. The reaction was quenched with sodium bicarbonate (15 mL), extracted with dichloromethane (3×50 mL), washed with brine, dried (sodium sulfate), filtered, and concentrated. Purification by column chromatography on silica gel using 30 to 100% ethyl acetate in hexanes afforded ethyl 2-(2,5-dimethyl-3-(2-(morpholinosulfonyl)benzoyl)-1H-pyrrol-1-yl)acetate (0.145 g, 0.334 mmol, 30% yield). 1H NMR (400 MHz, CDCl3): δ (ppm) 7.84 (d, 1H), 7.61 (app. t, 1H), 7.55 (dd, 1H), 7.39 (d, 1H), 5.72 (s, 1H), 4.51 (s, 2H), 4.23 (q, 2H), 3.68-3.71 (m, 4H), 3.14-3.17 (m, 4H), 2.44 (s, 3H), 2.07 (s, 3H), 1.29 (t, 3H).

Workup

  1. stirringThe reaction was stirred for 30 minutes at 0° C.
  2. temperatureto warm to room temperature
  3. stirringstirred for 3 hours at this temp
  4. customThe reaction was quenched with sodium bicarbonate (15 mL)
  5. extractionextracted with dichloromethane (3×50 mL)
  6. washwashed with brine
  7. dry with materialdried (sodium sulfate)
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customPurification by column chromatography on silica gel using 30 to 100% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-828b19e699c44a4fb97de02d45bc721a
Source dataset
uspto-grants-2014_03
Patent number
US08674115B2

Reaction notes

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