Methyl propiolate → methyl (E)-3-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-yl]-2-propenoate

HRID 2050574Notes

Reaction equation

HRID 2050574 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][C:5]([C:8]2[N:9]=[C:10]([CH:20]([CH3:22])[CH3:21])[NH:11][C:12]=2[C:13]2[CH:18]=[CH:17][C:16]([F:19])=[CH:15][CH:14]=2)=[CH:4][CH:3]=1.[C:23]([O:27][CH3:28])(=[O:26])[C:24]#[CH:25]>>[F:19][C:16]1[CH:17]=[CH:18][C:13]([C:12]2[N:11]=[C:10]([CH:20]([CH3:22])[CH3:21])[N:9](/[CH:25]=[CH:24]/[C:23]([O:27][CH3:28])=[O:26])[C:8]=2[C:5]2[CH:4]=[CH:3][C:2]([F:1])=[CH:7][CH:6]=2)=[CH:14][CH:15]=1

Participants

3

Reactant 2

HCID 13536Methyl propiolateHCID 148497764,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazole

Product 1

HCID 14849778methyl (E)-3-[4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazol-yl]-2-propenoateYield 46.6%

Procedure

From 4,5-bis(4-fluorophenyl)-2-(1-methylethyl)-1H-imidazole (2.00 g) and methyl propiolate (2.55 g) by the process as described for the preparation of Intermediate (7 a) to afford an orange solid which was purified by FCC eluting with System A (3:17) to afford the title compound (1.194 g) as a white solid. λmax (MeOH) 248.4 (22,180) and 300 (inf) nm (ε9410).

Workup

  1. customto afford an orange solid which
  2. customwas purified by FCC
  3. washeluting with System A (3:17)

Sources & evidence

ORD record
ord-55f9218a62e54a6ab4ee821c4adb871a
Source dataset
uspto-grants-1991_05
Patent number
US05013749

Reaction notes

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