Diisopropylethylamine → 3-(4-Pyrrolidin-1-ylmethylphenyl)propynoic acid-(4-prop-1-ynylphenyl)amide

HRID 734992Notes

Reaction equation

HRID 734992 reaction equation
C(N(C(C)C)C(C)C)C.I[C:11]1[CH:22]=[CH:21][C:14]([CH2:15][N:16]2[CH2:20][CH2:19][CH2:18][CH2:17]2)=[CH:13][CH:12]=1.[C:23]([C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:36])[C:34]#[CH:35])=[CH:28][CH:27]=1)#[C:24][CH3:25]>[Cu]I>[C:23]([C:26]1[CH:31]=[CH:30][C:29]([NH:32][C:33](=[O:36])[C:34]#[C:35][C:11]2[CH:22]=[CH:21][C:14]([CH2:15][N:16]3[CH2:20][CH2:19][CH2:18][CH2:17]3)=[CH:13][CH:12]=2)=[CH:28][CH:27]=1)#[C:24][CH3:25]

Participants

5

Reactant 3

HCID 81531DiisopropylethylamineHCID 185258671-(4-Iodobenzyl)pyrrolidineHCID 86060737Propynoic acid-(4-prop-1-ynylphenyl)amide2×

Product 1

HCID 578456773-(4-Pyrrolidin-1-ylmethylphenyl)propynoic acid-(4-prop-1-ynylphenyl)amide

Reagents, catalysts & solvents 1

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

Procedure

10 mL of acetonitrile is degassed and combined with 0.35 mL (2 mmol) of ethyldiisopropylamine and 0.2 g (0.69 mmol) of 1-(4-iodobenzyl)pyrrolidine. Then the mixture is again degassed and 13 mg of copper (I) iodide, 34 mg of tetrakistriphenylphosphine palladium, and 137 mg (0.75 mmol) of propynoic acid-(4-prop-1-ynylphenyl)amide are then added in succession. The reaction mixture is stirred for 24 hours at ambient temperature and then combined with 60 mg of propynoic acid-(4-prop-1-ynylphenyl)amide. After 24 hours, the mixture is evaporated down. The purification is carried out by column chromatography on silica gel (dichloromethane/methanol/ammonia (30:1:0.1 to 20:1:0.1)). Yield: 24 mg (10% of theory); C23H22N2O (M=342.44); calc.: molecular ion peak (M+H)+: 343; found: molecular ion peak (M+H)+: 343; Rf value: 0.2 (silica gel, dichloromethane/methanol/ammonia=10:1:0.1).

Workup

  1. custom10 mL of acetonitrile is degassed
  2. customThen the mixture is again degassed
  3. waitAfter 24 hours
  4. customthe mixture is evaporated down
  5. customThe purification

Sources & evidence

ORD record
ord-2692bdccfee544e8be4fc5cd1cb82eff
Source dataset
uspto-grants-2009_09
Patent number
US07592373B2

Reaction notes

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