Pyridine → HCID 19759258, compound

HRID 248378Notes

Reaction equation

HRID 248378 reaction equation
O[CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[C:12]([CH:14]=[CH2:15])[CH:11]=[C:10]2[C:16]#[N:17])=[CH:5][CH:4]=1.N1C=CC=CC=1.CS([Cl:28])(=O)=O>ClCCl.CN(C)C1C=CN=CC=1>[Cl:28][CH2:2][C:3]1[CH:8]=[CH:7][C:6]([N:9]2[CH:13]=[C:12]([CH:14]=[CH2:15])[CH:11]=[C:10]2[C:16]#[N:17])=[CH:5][CH:4]=1

Participants

6

Reactant 3

HCID 1049Pyridine2×HCID 31297Methanesulfonyl chloride2×HCID 19759464HCID 19759464, compound

Product 1

HCID 19759258HCID 19759258, compoundYield 84.4%

Reagents, catalysts & solvents 2

HCID 142844-(Dimethylamino)pyridineCatalystHCID 6344DichloromethaneSolvent

Procedure

To a solution of 1-(4-hydroxymethylphenyl)-4-vinylpyrrole-2-carbonitrile (910 mg) in dichloromethane (15 ml) was added pyridine (385 mg), 4-dimethylaminopyridine (20 mg), methanesulfonyl chloride (560 mg) successively at 5° C. The mixture was stirred at ambient temperature for 4 hours and then pyridine (385 mg) and methanesulfonyl chloride (560 mg) was added therein. The mixture was stirred at the same temperature overnight, washed with aqueous hydrochloric acid, dried, and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel eluted by dichloromethane to yield 1-(4-chloromethylphenyl)-4-vinylpyrrole-2-carbonitrile (831 mg) as a colorless oil.

Workup

  1. stirringThe mixture was stirred at the same temperature overnight
  2. washwashed with aqueous hydrochloric acid
  3. customdried
  4. concentrationconcentrated in vacuo
  5. customThe residue was purified by flash column chromatography on silica gel
  6. washeluted by dichloromethane

Sources & evidence

ORD record
ord-3f4a96ceebed403d809a6dc768b4827c
Source dataset
uspto-grants-1993_05
Patent number
US05210092

Reaction notes

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