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29th November 2012 @ 23:45
Upscaled synthesis of 1-ethoxy-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate through formation of ester bond between 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylic acid and ethyl 2-bromopropanoate.

4123.png

Reaction start time: 5:20 PM EST 28/11/12
MRN 57-1 (1.0 g, was dissolved in DMF (20 mL), then Potassium Carbonate (1.5 g) was added after. The mixture was stirred at room temperature for 20 minutes, followed by addition of Ethyl-2-bromopropionate (0.76 mL, ) and was left stirring overnight at room temperature.

At 12:00 PM ethyl acetate:water (60 mL, 1:1) mixture was added to the reaction and extracted with ethyl acetate (3 × 20 mL) the organic layers were combined, washed with water (20 mL), brine (20 mL), then dried over magnesium sulfate and concentrated to a brown oil, which was left to dry under high vac for 5 hours.

Risk and Hazard assessment:
Same as Upscaled synthesis of 1-ethoxy-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate (MD 17-2).
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26th November 2012 @ 04:46
EDCI coupling of 2-bromopropionic acid with ammonia solution to form MD 20-1 that can then be coupled with 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylic acid.

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Reaction start time: 1:40 PM EST 26/11/12
HOBt (0.096 g, 0 mmol) and EDCI (0.11 g, 6.0 mmol, 1.2 equiv.) were added to a solution of 2-bromopropionic acid (0.45 mL,) in DCM (5 mL) after 20 minutes of stirring, after which 28% Ammonia(aq) (0.28 mL, 7.5 mmol, 1.5 equiv.) was added and the reaction stirred at room temperature.

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Risk and Hazard assessment:
RA
26th November 2012 @ 01:24
Upscaled synthesis of 1-ethoxy-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate through formation of ester bond between 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylic acid and ethyl 2-bromopropanoate.

4123.png

Reaction start time: 12:20 PM EST 26/11/12
MRN 57-1 (2.0 g, was dissolved in DMF (30 mL), then Potassium Carbonate (3.0 g) was added after. The mixture was stirred at room temperature for 20 minutes, followed by addition of Ethyl-2-bromopropionate (1.5 mL, ) and was left stirring overnight at room temperature.

At 12:00 PM Ethyl acetate:water (80 mL, 1:1) mixture was added to the reaction and extracted with ethyl acetate (3 × 20 mL) the organic layers were combined, dried over magnesium sulfate and concentrated under reduced atmosphere to give a dark brown liquid. The organic layer was washed with water again to remove any remaining DMF (2 × 30 mL), dried over magnesium sulfate and concentrated to a dark brown oil, which was left to dry over night. In the morning light brown crystals had formed (0.73 g,).

Risk and Hazard assessment:
Same as Synthesis of 1-ethoxy-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate through ester synthesis (MD 17-1) but with increased quantities of reagents.
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23rd November 2012 @ 02:59
EDCI coupling of 2-bromopropionic acid with ammonia solution to form MD 20-1 that can then be coupled with 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylic acid.

4245.png

Reaction start time: 3:50 PM EST 23/11/12
HOBt (0.086 g, 0.64 mmol) and EDCI (0.11 g, 6.0 mmol, 1.2 equiv.) were added to a solution of 2-bromopropionic acid (0.45 mL,) in DCM (5 mL) after 20 minutes of stirring, after which 28% Ammonia(aq) (0.28 mL, 7.5 mmol, 1.5 equiv.) was added and the reaction stirred at room temperature.

See also:

Risk and Hazard assessment:
RA
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23rd November 2012 @ 02:25
Synthesis of 2-((1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carbonyl)oxy)propanoic acid

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Reaction start time: 5:32 PM EST 22/11/12
MRN 57-1 (0.23 g, 1 mmol,) was dissolved in DMF (6 mL), potassium carbonate (0.5 g,) was added and the mixture was stirred for 30 minutes at room temperature after which 2-bromopropionic acid (120 µL, 1.3 mmol,), TLC at 8 PM showed the presence of starting material.

See also:

Risk and Hazard assessment:
Same as Synthesis of 1-ethoxy-1-oxopropan-2-yl 1-(4-fluorophenyl)-2,5-dimethyl-1H-pyrrole-3-carboxylate through ester synthesis (MD 17-1),exception is 2-bromopropionic acid is corrosive and causes severe burns.
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