4-Iodo-1-tritylimidazole → 1-isoquinolin-1-yl-1-(1-trityl-1H-imidazol-4-yl)-ethanol

HRID 748658

Reaction equation

HRID 748658 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.[C:30]1([C:40](=[O:42])[CH3:41])[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][N:31]=1>ClCCl>[C:30]1([C:40]([C:2]2[N:3]=[CH:4][N:5]([C:7]([C:8]3[CH:13]=[CH:12][CH:11]=[CH:10][CH:9]=3)([C:20]3[CH:21]=[CH:22][CH:23]=[CH:24][CH:25]=3)[C:14]3[CH:19]=[CH:18][CH:17]=[CH:16][CH:15]=3)[CH:6]=2)([OH:42])[CH3:41])[C:39]2[C:34](=[CH:35][CH:36]=[CH:37][CH:38]=2)[CH:33]=[CH:32][N:31]=1

Participants

5

Reactant 3

HCID 6182524-Iodo-1-tritylimidazoleHCID 131572141-(Isoquinolin-1-yl)ethan-1-oneHCID 178418443HCID 178418443, compound

Product 1

HCID 597514831-isoquinolin-1-yl-1-(1-trityl-1H-imidazol-4-yl)-ethanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A mixture of 4-iodo-1-tritylimidazole (commercially available) (15.5 g, 35.4 mmol) in dichloromethane (80 mL) at 20° C. was treated with ethyl magnesium bromide (12.0 mL, 36 mmol, 3M in ether) and allowed to react for 1 h. A solution of 1-isoquinolin-1-yl-ethanone (Intermediate H2) (3.65 g, 21.3 mmol) in dichloromethane (20 mL) was added via addition funnel at 20° C. and stirred for 16 h. The mixture was quenched with sat. ammonium chloride (100 mL) and diluted with dichloromethane. The residue was isolated in an aqueous workup. The product was extracted with CH2Cl2 and purified by chromatography on silica gel with 5% NH3-MeOH: CH2Cl2 to give 1-isoquinolin-1-yl-1-(1-trityl-1H-imidazol-4-yl)-ethanol (Intermediate H3) as a solid.

Workup

  1. customto react for 1 h
  2. customThe mixture was quenched with sat. ammonium chloride (100 mL)
  3. additiondiluted with dichloromethane
  4. customThe residue was isolated in an aqueous workup
  5. extractionThe product was extracted with CH2Cl2
  6. custompurified by chromatography on silica gel with 5% NH3-MeOH

Sources & evidence

ORD record
ord-233ecd94c5474dd7a7ef2c8171474ec3
Source dataset
uspto-grants-2008_07
Patent number
US07399868B2

Linked notes

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