Tri(butyl)vinylstannane → N-[(4-chlorophenyl)methyl]-1-methyl-4-oxo-6-vinyl-quinoline-3-carboxamide

HRID 1067998Notes

Reaction equation

HRID 1067998 reaction equation
[CH2:1](C([SnH3])=C(CCCC)CCCC)[CH2:2]CC.[Cl:16][C:17]1[CH:39]=[CH:38][C:20]([CH2:21][NH:22][C:23]([C:25]2[C:34](=[O:35])[C:33]3[C:28](=[CH:29][CH:30]=[C:31](I)[CH:32]=3)[N:27]([CH3:37])[CH:26]=2)=[O:24])=[CH:19][CH:18]=1>Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.O>[Cl:16][C:17]1[CH:39]=[CH:38][C:20]([CH2:21][NH:22][C:23]([C:25]2[C:34](=[O:35])[C:33]3[C:28](=[CH:29][CH:30]=[C:31]([CH:1]=[CH2:2])[CH:32]=3)[N:27]([CH3:37])[CH:26]=2)=[O:24])=[CH:19][CH:18]=1

Participants

5

Reactant 2

HCID 21115800Tri(butyl)vinylstannaneHCID 21192528N-(4-Chlorobenzyl)-6-iodo-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide

Product 1

HCID 16073870N-[(4-chlorophenyl)methyl]-1-methyl-4-oxo-6-vinyl-quinoline-3-carboxamideYield 57%

Reagents, catalysts & solvents 2

HCID 178418476HCID 178418476, compoundCatalystHCID 962WaterSolvent

Procedure

Tributylvinylstannane (0.32 mL) is added to a solution of N-(4-chlorobenzyl)-6-iodo-1-methyl-4-oxo-1,4-dihydro-3-quinolinecarboxamide (0.45 g) from Preparation No. 39 and PdCl2(PPh3)2 (70 mg). The mixture is stirred at room temperature for 1 h and then is heated to 60° C. for 30 min. After cooling to room temperature, the reaction mixture is poured into water (60 mL), filtered, and washed with water (20 mL) and diethyl ether (20 mL). The crude product is purified by recrystallization from acetonitrile to afford 0.20 g (57%) of the title compound as a white solid.

Workup

  1. temperatureis heated to 60° C. for 30 min
  2. temperatureAfter cooling to room temperature
  3. filtrationfiltered
  4. washwashed with water (20 mL) and diethyl ether (20 mL)
  5. customThe crude product is purified by recrystallization from acetonitrile

Sources & evidence

ORD record
ord-6533be7524704bf28a2654879f32d684
Source dataset
uspto-grants-2001_06
Patent number
US06248739B1

Reaction notes

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