Pyridinium, 1-amino-, iodide (1:1) → HCID 21948674, compound

HRID 2214925Notes

Reaction equation

HRID 2214925 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]#[C:9][C:10]([O:12][CH3:13])=[O:11])=[CH:4][CH:3]=1.[I-].[NH2:15][N+:16]1[CH:21]=[CH:20][CH:19]=[CH:18][CH:17]=1.N1(C2CCCCCCCCCC2)CCCN=CCCCCC1>C(#N)C>[F:1][C:2]1[CH:3]=[CH:4][C:5]([C:8]2[C:9]([C:10]([O:12][CH3:13])=[O:11])=[C:17]3[CH:18]=[CH:19][CH:20]=[CH:21][N:16]3[N:15]=2)=[CH:6][CH:7]=1

Participants

5

Reactant 3

HCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 111268212-Propynoic acid, 3-(4-fluorophenyl)-, methyl esterHCID 1296629601,8-Diazabicycloundec-7ene

Product 1

HCID 21948674HCID 21948674, compound

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent2×

Procedure

A stirred solution of methyl 3-(4-fluorophenyl)propiolate (8.02 g, 45 mmol) and 1-aminopyridinium iodide (10 g, 45 mmol) in dry acetonitrile (150 mL) was cooled to about 0° C. A solution of 1,8-diazabicycloundec-7-ene (13.7 g, 90 mmol) in dry acetonitrile (50 mL) was added dropwise over 1 hour. The mixture was allowed to stir at room temperature for about 18 h. The reaction mixture was cooled in an ice bath for about 30 minutes and the precipitate was collected by filtration and washed with cold acetonitrile (10 mL). The solid was dried under reduced pressure to give the title compound as a white solid, 8.48 g (70%). 1H NMR (CDCl3) δ 8.50 (d, 1H, J=8.4 Hz), 8.18 (d, 1H, J=8.8 Hz), 7.78 (m, 2H), 7.42 (t, 1H, J=8.4 Hz), 7.13 (t, 2H, J=8.8 Hz), 6.97 (td, 1H, J=6.8, 1 Hz).). MS (+ve ion electrospray) 271 (100), (MH+).

Workup

  1. temperatureThe reaction mixture was cooled in an ice bath for about 30 minutes
  2. filtrationthe precipitate was collected by filtration
  3. washwashed with cold acetonitrile (10 mL)
  4. customThe solid was dried under reduced pressure

Sources & evidence

ORD record
ord-c08e0970fc9e437a8e0add6014336427
Source dataset
uspto-grants-2006_09
Patent number
US07109209B2

Reaction notes

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