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

HRID 892954

Reaction equation

HRID 892954 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 (7a) 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-22117a741d364abd9b86c06237b36e6c
Source dataset
uspto-grants-1992_06
Patent number
US05120848

Linked notes

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