Potassium Carbonate → HCID 89826032, compound

HRID 2272984Notes

Reaction equation

HRID 2272984 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[NH:7][CH:8]=[C:9]([F:11])[CH:10]=1)=[O:5])[CH3:2].Br[CH2:13][C:14]([C:16]1[CH:21]=[CH:20][C:19]([CH:22]2[CH2:27][CH2:26][N:25]([C:28](=[O:33])[C:29]([F:32])([F:31])[F:30])[CH2:24][CH2:23]2)=[CH:18][CH:17]=1)=[O:15].C(=O)([O-])[O-].[K+].[K+]>CC(C)=O>[CH2:1]([O:3][C:4]([C:6]1[N:7]([CH2:13][C:14](=[O:15])[C:16]2[CH:21]=[CH:20][C:19]([CH:22]3[CH2:27][CH2:26][N:25]([C:28](=[O:33])[C:29]([F:32])([F:30])[F:31])[CH2:24][CH2:23]3)=[CH:18][CH:17]=2)[CH:8]=[C:9]([F:11])[CH:10]=1)=[O:5])[CH3:2]

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 72212396HCID 72212396, compoundHCID 88153670HCID 88153670, compound

Product 1

HCID 89826032HCID 89826032, compound

Reagents, catalysts & solvents 1

HCID 180AcetoneSolvent2×

Procedure

4-Fluoro-1H-pyrrole-2-carboxylic acid ethyl ester (1.07 g; 6.83 mmol) and 1-{4-[4-(2-bromo-acetyl)-phenyl]-piperidin-1-yl}-2,2,2-trifluoro-ethanone (2.00 g; 5.26 mmol) are dissolved in acetone (20 ml). To this clear brown solution potassium carbonate (1.45 g; 10.51 mmol) is added and the reaction mixture is stirred at ambient temperature over night. The reaction mixture is diluted with acetone, filtered off by suction and washed with acetone. The filtrate is evaporated to dryness. The crude product is purified by flashchromatography to afford 4-fluoro-1-(2-oxo-2-{4-[1-(2,2,2-trifluoro-acetyl)-piperidin-4-yl]-phenyl}-ethyl)-1H-pyrrole-2-carboxylic acid ethyl ester as off-white solid; HPLC/MS 2.67 min (A), [M+H] 455.

Workup

  1. filtrationfiltered off by suction
  2. washwashed with acetone
  3. customThe filtrate is evaporated to dryness
  4. customThe crude product is purified by flashchromatography

Sources & evidence

ORD record
ord-0c4b6e2a7f1b43499fc343675517f784
Source dataset
uspto-grants-2015_09
Patent number
US09120805B2

Reaction notes

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