Water → HCID 86746856, compound

HRID 248929Notes

Reaction equation

HRID 248929 reaction equation
[CH2:1]([C:5]1[NH:6][CH:7]=[C:8]([CH:10]=[CH:11][C:12]([O:14][CH3:15])=[O:13])[CH:9]=1)[CH2:2][CH2:3][CH3:4].[H-].[Na+].[C:18]([C:20]1[CH:25]=[CH:24][CH:23]=[CH:22][C:21]=1[C:26]1[CH:31]=[CH:30][C:29]([CH2:32]Br)=[CH:28][CH:27]=1)#[N:19].O>CN(C=O)C>[CH2:1]([C:5]1[N:6]([CH2:32][C:29]2[CH:28]=[CH:27][C:26]([C:21]3[CH:22]=[CH:23][CH:24]=[CH:25][C:20]=3[C:18]#[N:19])=[CH:31][CH:30]=2)[CH:7]=[C:8]([CH:10]=[CH:11][C:12]([O:14][CH3:15])=[O:13])[CH:9]=1)[CH2:2][CH2:3][CH3:4]

Participants

6

Reactant 4

HCID 962WaterHCID 24758Sodium hydrideHCID 15019124'-(Bromomethyl)-2-cyanobiphenylHCID 54396318HCID 54396318, compound

Product 1

HCID 86746856HCID 86746856, compoundYield 76.9%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Conditions

Temperature
0 °C

Procedure

Methyl 3-[2-(n-butyl)pyrrol-4-yl]acrylate (AE) (6.2 g) (prepared, e.g., as described in Preparation 21), in DMF (200 ml) was treated with sodium hydride (1.8 g of 60% mineral oil dispersion) at 0° C., and the resulting mixture was stirred for 30 minutes at 0° C. 2'-(Cyano)biphenyl-4-ylmethyl bromide (9.8 g) was added, and the mixture allowed to come to room temperature. Water was added, and the mixture was extracted with ethyl acetate. The ethyl acetate extract was washed with water, brine, dried over sodium sulfate and evaporated. The residue was chromatographed on silica gel, eluting with 25% ethyl acetate/hexane, affording methyl 3-[2-(n-butyl)-1-(2"-cyanobiphenyl-4'-ylmethyl)pyrrol-4-yl]acrylate (9.17 g), a compound of Formula AF, as an oil.

Workup

  1. customto come to room temperature
  2. extractionthe mixture was extracted with ethyl acetate
  3. extractionThe ethyl acetate extract
  4. washwas washed with water, brine
  5. dry with materialdried over sodium sulfate
  6. customevaporated
  7. customThe residue was chromatographed on silica gel
  8. washeluting with 25% ethyl acetate/hexane

Sources & evidence

ORD record
ord-1d9b97abdd284e34b8cc8481a9b6591b
Source dataset
uspto-grants-1993_05
Patent number
US05212195

Reaction notes

Loading…