Pyridine → HCID 18786088, compound

HRID 1107848Notes

Reaction equation

HRID 1107848 reaction equation
[Br-:1].[NH2:2][C:3]1[CH:8]=[C:7]([F:9])[CH:6]=[CH:5][C:4]=1[CH2:10][P+:11]([C:24]1[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=1)([C:18]1[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1)[C:12]1[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=1.[C:30](Cl)(=[O:33])[CH:31]=[CH2:32].N1C=CC=CC=1>C(Cl)Cl>[Br-:1].[F:9][C:7]1[CH:6]=[CH:5][C:4]([CH2:10][P+:11]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)([C:12]2[CH:17]=[CH:16][CH:15]=[CH:14][CH:13]=2)[C:18]2[CH:19]=[CH:20][CH:21]=[CH:22][CH:23]=2)=[C:3]([NH:2][C:30](=[O:33])[CH:31]=[CH2:32])[CH:8]=1

Participants

5

Reactant 3

HCID 1049PyridineHCID 13140Acryloyl chlorideHCID 18786085HCID 18786085, compound

Product 1

HCID 18786088HCID 18786088, compoundYield 81%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A suspension of 89 g (0.19 mol) of [(2-amino-4-fluorophenyl)methyl]-triphenylphosphonium bromide in 1.5 L CH2Cl2 was stirred and 17 mL (0.21 mol) of acryloyl chloride was added dropwise. A 22.8 mL sample of pyridine was added dropwise. The mixture was heated under reflux for 45 min. The mixture was cooled, washed with K2CO3 solution, dilute hydrochloric acid and brine. It was dried (Na2SO4), concentrated and triturated with Et2O to give 80 g (81%) of [[4-fluoro-2-[(1-oxo-2-propenyl)amino]phenyl]methyl]triphenylphosphonium bromide as a yellowish solid: 1H NMR (CDCl3) δ 8.0-7.4 (m, 15H); 6.9 (m, 2H); 6.4 (m, 1H); 6.1 (d, 1H); 5.9 (d, 2H); 5.5 (d, 1H). ##STR18##

Workup

  1. temperatureThe mixture was heated
  2. temperatureunder reflux for 45 min
  3. temperatureThe mixture was cooled
  4. washwashed with K2CO3 solution, dilute hydrochloric acid and brine
  5. dry with materialIt was dried (Na2SO4)
  6. concentrationconcentrated
  7. customtriturated with Et2O

Sources & evidence

ORD record
ord-8f7d112b6a1b4b9eb7ffa85821a68179
Source dataset
uspto-grants-2000_05
Patent number
US06063803

Reaction notes

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