4-Iodo-1-tritylimidazole → 2-phenyl-l-(1-trityl-1H-imidazol-4-yl)ethanone

HRID 1028195Notes

Reaction equation

HRID 1028195 reaction equation
I[C:2]1[N:3]=[CH:4][N:5]([C:7]([C:20]2[CH:25]=[CH:24][CH:23]=[CH:22][CH:21]=2)([C:14]2[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=2)[C:8]2[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=2)[CH:6]=1.C([Mg]Br)C.CON(C)[C:33](=[O:41])[CH2:34][C:35]1[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1>ClCCl>[C:35]1([CH2:34][C:33]([C:2]2[N:3]=[CH:4][N:5]([C:7]([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)([C:14]3[CH:15]=[CH:16][CH:17]=[CH:18][CH:19]=3)[C:8]3[CH:9]=[CH:10][CH:11]=[CH:12][CH:13]=3)[CH:6]=2)=[O:41])[CH:40]=[CH:39][CH:38]=[CH:37][CH:36]=1

Participants

5

Reactant 3

HCID 6182524-Iodo-1-tritylimidazoleHCID 10419762N-Methoxy-N-methyl-2-phenylacetamideHCID 178418443HCID 178418443, compound

Product 1

HCID 574376792-phenyl-l-(1-trityl-1H-imidazol-4-yl)ethanone

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 4-iodo-l-tritylimidazole (commercially available, 5.08 g, 13.7 mmol) in dichloromethane (100 mL) at −10° C. was treated with ethylmagnesium bromide (4.5 mL, 13.7 mmol, 3M in ether) and allowed to react for 45 m. A solution of N-methoxy-N-methyl-2-phenylacetamide, (Intermediate 13) (2.0 g, 11.2 mmol) in dichloromethane was added via syringe at −10° C. and stirred for 16 hours at room temperature. The mixture was quenched with water (50 mL) and a saturated solution of ammonium chloride (50 mL). The residue was isolated in a typical aqueous workup and purified by MPLC with 3 to 5% MeOH:CH2Cl2 to give 2-phenyl-l-(1-trityl-1H-imidazol-4-yl)ethanone, (Intermediate 14) as a solid, (4.65 g).

Workup

  1. customto react for 45 m
  2. customThe mixture was quenched with water (50 mL)
  3. customThe residue was isolated in a typical aqueous workup
  4. custompurified by MPLC with 3 to 5% MeOH

Sources & evidence

ORD record
ord-3d1c043369814b8dac7579a07de21f33
Source dataset
uspto-grants-2014_05
Patent number
US08735438B2

Reaction notes

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