Cesium carbonate → 3-[4-(2-Pyrrolidin-1-ylethyl)phenyl]propynoic acid-biphenyl-4-ylamide

HRID 735026Notes

Reaction equation

HRID 735026 reaction equation
I[C:2]1[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]2[CH2:14][CH2:13][CH2:12][CH2:11]2)=[CH:4][CH:3]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[C:21]1([C:32]2[CH:37]=[CH:36][CH:35]=[CH:34][CH:33]=2)[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:31])[C:29]#[CH:30])=[CH:23][CH:22]=1>[Cu]I>[C:21]1([C:32]2[CH:33]=[CH:34][CH:35]=[CH:36][CH:37]=2)[CH:26]=[CH:25][C:24]([NH:27][C:28](=[O:31])[C:29]#[C:30][C:2]2[CH:7]=[CH:6][C:5]([CH2:8][CH2:9][N:10]3[CH2:14][CH2:13][CH2:12][CH2:11]3)=[CH:4][CH:3]=2)=[CH:23][CH:22]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 688158361-(4-Iodophenethyl)pyrrolidineHCID 86060713Propynoic acid-biphenyl-4-ylamide

Product 1

HCID 578457013-[4-(2-Pyrrolidin-1-ylethyl)phenyl]propynoic acid-biphenyl-4-ylamide

Reagents, catalysts & solvents 1

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)Catalyst

Procedure

25 mL of THF are degassed and combined with 0.25 g (0.83 mmol) of 1-[2-(4-iodophenyl)ethyl]pyrrolidine, 0.81 g (2.49 mmol) of cesium carbonate, 16 mg (0.083 mmol) of copper (I) iodide and 38 mg (0.033 mmol) of tetrakistriphenylphosphine palladium. Then the mixture is again degassed, and 184 mg (0.83 mmol) of propynoic acid-biphenyl-4-ylamide are added. The reaction mixture is stirred for 3 hours at ambient temperature, poured onto water and extracted with ethyl acetate. The organic phase is extracted three times with water and dried over sodium sulfate. The purification is carried out by column chromatography on silica gel (dichloromethane/methanol/ammonia=10:1:0.1)). Yield: 90 mg (27.5% of theory); melting point: 180-189° C.; C27H26N2O (M=394.52); calc.: molecular ion peak (M+H)+: 395; found: molecular ion peak (M+H)+: 395.

Workup

  1. custom25 mL of THF are degassed
  2. customThen the mixture is again degassed
  3. additionpoured onto water
  4. extractionextracted with ethyl acetate
  5. extractionThe organic phase is extracted three times with water
  6. dry with materialdried over sodium sulfate
  7. customThe purification

Sources & evidence

ORD record
ord-522583451aa741fab7993b1a81b520d2
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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