Tributylamine → HCID 68830753, compound

HRID 747730Notes

Reaction equation

HRID 747730 reaction equation
[C:1]([C:3]1[CH:4]=[CH:5][C:6](I)=[C:7]([CH:34]=1)[O:8][CH2:9][CH2:10][NH:11][C:12](=[O:33])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH:20]2[CH2:25][CH2:24][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:22][CH2:21]2)=[CH:15][CH:14]=1)#[N:2].[NH:36]([C:40](=[CH2:45])[C:41]([O:43][CH3:44])=[O:42])[C:37]([CH3:39])=[O:38].C1(C)C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C.C(N(CCCC)CCCC)CCC>C(#N)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[C:37]([NH:36][C:40](=[CH:45][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[CH:34][C:7]=1[O:8][CH2:9][CH2:10][NH:11][C:12](=[O:33])[C:13]1[CH:18]=[CH:17][C:16]([O:19][CH:20]2[CH2:21][CH2:22][N:23]([C:26]([O:28][C:29]([CH3:32])([CH3:31])[CH3:30])=[O:27])[CH2:24][CH2:25]2)=[CH:15][CH:14]=1)[C:41]([O:43][CH3:44])=[O:42])(=[O:38])[CH3:39]

Participants

7

Reactant 4

HCID 7622TributylamineHCID 80271Tri-o-tolylphosphineHCID 98644Methyl 2-acetamidoacrylateHCID 68830389HCID 68830389, compound

Product 1

HCID 68830753HCID 68830753, compound

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6342AcetonitrileSolvent

Procedure

2.72 g (4.60 mmol) of N-[2-(5-cyano-2-iodophenoxy)ethyl]-4-(1-t-butoxycarbonyl-4-piperidyloxy)benzamide and 1.32 g (9.22 mmol) of methyl 2-acetaminoacrylate were dissolved in 80 ml of acetonitrile. 272 mg (1.21 mmol) of palladium (II) acetate, 630 mg (2.07 mmol) of tri-o-tolylphosphine and 1.71 g (9.23 mmol) of tributylamine were added to the solution, and they were heated under reflux for 3 days. The solvent was evaporated, and the residue was treated with ethyl acetate as the extractant in an ordinary manner to obtain the crude product, which was purified by the silica gel column chromatography to obtain the title compound.

Workup

  1. temperaturewere heated
  2. temperatureunder reflux for 3 days
  3. customThe solvent was evaporated
  4. additionthe residue was treated with ethyl acetate as the extractant in an ordinary manner
  5. customto obtain the crude product, which
  6. customwas purified by the silica gel column chromatography

Sources & evidence

ORD record
ord-40ff9b6a935046af95fdd547548eca27
Source dataset
uspto-grants-2008_07
Patent number
US07396844B1

Reaction notes

Loading…