Methyl iodide → 2-Methyl-1-(1-methyl-1H-indol-3-yl)-3-[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]-1-propanone

HRID 1382787Notes

Reaction equation

HRID 1382787 reaction equation
O1CCC[CH2:2]1.C(NC(C)C)(C)C.[Li].[CH3:14][N:15]1[C:23]2[C:18](=[CH:19][CH:20]=[CH:21][CH:22]=2)[C:17]([C:24](=[O:52])[CH2:25][CH2:26][C:27]2[N:28]=[CH:29][N:30]([C:33]([C:46]3[CH:51]=[CH:50][CH:49]=[CH:48][CH:47]=3)([C:40]3[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=3)[C:34]3[CH:39]=[CH:38][CH:37]=[CH:36][CH:35]=3)[C:31]=2[CH3:32])=[CH:16]1.IC.C(=O)([O-])[O-].[K+].[K+]>C1COCC1.O.C(O)(=O)C>[CH3:2][CH:25]([CH2:26][C:27]1[N:28]=[CH:29][N:30]([C:33]([C:34]2[CH:35]=[CH:36][CH:37]=[CH:38][CH:39]=2)([C:46]2[CH:47]=[CH:48][CH:49]=[CH:50][CH:51]=2)[C:40]2[CH:45]=[CH:44][CH:43]=[CH:42][CH:41]=2)[C:31]=1[CH3:32])[C:24]([C:17]1[C:18]2[C:23](=[CH:22][CH:21]=[CH:20][CH:19]=2)[N:15]([CH3:14])[CH:16]=1)=[O:52]

Participants

8

Reactant 4

HCID 6328Methyl iodide2×HCID 11430Potassium CarbonateHCID 212732461-(1-methyl-1H-indol-3-yl)-3-[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]-1-propanoneHCID 68798419Lithium diisopropylamine mono(tetrahydrofuran)

Product 1

HCID 212732302-Methyl-1-(1-methyl-1H-indol-3-yl)-3-[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]-1-propanone

Reagents, catalysts & solvents 3

HCID 176Acetic AcidSolventHCID 962WaterSolventHCID 8028TetrahydrofuranSolvent

Procedure

Lithium diisopropylamine mono(tetrahydrofuran) (1.5M in cyclohexane, 11.5 ml) was added dropwise to a cold (-70°) solution of 1-(1-methyl-1H-indol-3-yl)-3-[5-methyl-1-(triphenylmethyl)-1H-imidazol-4-yl]-1-propanone (8.8 g) in dry THF (175 ml) under nitrogen. The stirred solution was allowed to warm to 20° over 1 h then cooled to -70°. Iodomethane (2.15 ml) was added and the mixture was allowed to reach 20° over 1 h and stirred for a further 2 h. More iodomethane (1.08 ml) was added and stirring was continued for 2 h. The mixture was treated with acetic acid (10 ml) and water (10 ml), poured into saturated potassium carbonate solution (200 ml) and extracted with ethyl acetate (2×100 ml). The combined, dried organic extracts were filtered and evaporated to give a yellow foam (11.3 g). FCC (column made up of EtOAc:Et3N 99:1) eluting with ethyl acetate gave the title compound (5.0 g) as a white solid, m.p. 209°-210°.

Workup

  1. temperatureto warm to 20° over 1 h
  2. temperaturethen cooled to -70°
  3. stirringstirring
  4. waitwas continued for 2 h
  5. extractionextracted with ethyl acetate (2×100 ml)
  6. filtrationdried organic extracts were filtered
  7. customevaporated

Sources & evidence

ORD record
ord-b3421a99c0f6418f917f1ba77731a313
Source dataset
uspto-grants-1989_02
Patent number
US04808581

Reaction notes

Loading…