2-Iodopyridine → pyridin-2-yl(quinolin-8-yl)(1-trityl-1H-imidazol-5-yl)methanol

HRID 390362Notes

Reaction equation

HRID 390362 reaction equation
I[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][N:3]=1.C([Mg]Br)C.[N:12]1[C:21]2[C:16](=[CH:17][CH:18]=[CH:19][C:20]=2[C:22]([C:24]2[N:28]([C:29]([C:42]3[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=3)([C:36]3[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=3)[C:30]3[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=3)[CH:27]=[N:26][CH:25]=2)=[O:23])[CH:15]=[CH:14][CH:13]=1>ClCCl>[N:3]1[CH:4]=[CH:5][CH:6]=[CH:7][C:2]=1[C:22]([C:20]1[CH:19]=[CH:18][CH:17]=[C:16]2[C:21]=1[N:12]=[CH:13][CH:14]=[CH:15]2)([C:24]1[N:28]([C:29]([C:36]2[CH:41]=[CH:40][CH:39]=[CH:38][CH:37]=2)([C:42]2[CH:47]=[CH:46][CH:45]=[CH:44][CH:43]=2)[C:30]2[CH:31]=[CH:32][CH:33]=[CH:34][CH:35]=2)[CH:27]=[N:26][CH:25]=1)[OH:23]

Participants

5

Reactant 3

HCID 2211262-IodopyridineHCID 59419663quinolin-8-yl(1-trityl-1H-imidazol-5-yl)methanoneHCID 178418443HCID 178418443, compound

Product 1

HCID 59419684pyridin-2-yl(quinolin-8-yl)(1-trityl-1H-imidazol-5-yl)methanol

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

A solution of 2-iodo-pyridine (commercially available) (307 mg, 1.5 mmol) in dichloromethane (20 mL) at room temperature was treated with ethyl magnesium bromide (0.50 mL, 1.5 mmol, 3M in ether) and allowed to react for 45 m. A solution quinolin-8-yl(1-trityl-1H-imidazol-5-yl)methanone, (Intermediate 13) (465 mg, 1.00 mmol) in dichloromethane was added via syringe at room temperature and the reaction mixture was then stirred at room temperature for 16 h. The mixture was quenched with water (20 mL) and a sat. solution of ammonium chloride (20 mL). The residue was isolated in a typical aqueous to give pyridin-2-yl(quinolin-8-yl)(1-trityl-1H-imidazol-5-yl)methanol, (Intermediate 14) (385 mg, crude).

Workup

  1. customto react for 45 m
  2. customThe mixture was quenched with water (20 mL)
  3. customThe residue was isolated in a typical aqueous

Sources & evidence

ORD record
ord-84cb8b50a1194bc4a79dd36b9ac11729
Source dataset
uspto-grants-2013_02
Patent number
US08383646B2

Reaction notes

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