Chloroiodomethane → HCID 178438609, compound

HRID 1412315Notes

Reaction equation

HRID 1412315 reaction equation
[CH2:1]([Zn]CC)C.ClCI.[Si:9]([O:16][C:17](=[CH2:55])[CH2:18][O:19][C@H:20]1[CH2:25][CH2:24][C@H:23]([N:26]2[C:31](=[O:32])[C:30]([CH2:33][C:34]3[CH:39]=[CH:38][C:37]([C:40]4[C:41]([C:46]#[N:47])=[CH:42][CH:43]=[CH:44][CH:45]=4)=[CH:36][CH:35]=3)=[C:29]([CH2:48][CH2:49][CH3:50])[N:28]3[N:51]=[C:52]([CH3:54])[N:53]=[C:27]23)[CH2:22][CH2:21]1)([C:12]([CH3:15])([CH3:14])[CH3:13])([CH3:11])[CH3:10].[Cl-].[NH4+]>C(Cl)Cl>[Si:9]([O:16][C:17]1([CH2:18][O:19][C@H:20]2[CH2:21][CH2:22][C@H:23]([N:26]3[C:31](=[O:32])[C:30]([CH2:33][C:34]4[CH:39]=[CH:38][C:37]([C:40]5[C:41]([C:46]#[N:47])=[CH:42][CH:43]=[CH:44][CH:45]=5)=[CH:36][CH:35]=4)=[C:29]([CH2:48][CH2:49][CH3:50])[N:28]4[N:51]=[C:52]([CH3:54])[N:53]=[C:27]34)[CH2:24][CH2:25]2)[CH2:1][CH2:55]1)([C:12]([CH3:14])([CH3:15])[CH3:13])([CH3:11])[CH3:10]

Participants

6

Reactant 4

HCID 11644ChloroiodomethaneHCID 25517Ammonium ChlorideHCID 178418750HCID 178418750, compoundHCID 178459262HCID 178459262, compound

Product 1

HCID 178438609HCID 178438609, compoundYield 52%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent3×

Procedure

To a solution (10 mL) of diethylzinc (1.0 M hexane solution, 5.3 mL) in methylene chloride was added a solution (5 mL) of chloro(iodo)methane (0.38 mL) in methylene chloride at 0° C., and the mixture was stirred at the same temperature for 10 min. A solution (5 mL) of 4′-[(4-{trans-4-[(2-{[tert-butyl(dimethyl)silyl]oxy}prop-2-en-1-yl)oxy]cyclohexyl}-2-methyl-5-oxo-7-propyl-4,5-dihydro[1,2,4]triazolo[1,5-a]pyrimidin-6-yl)methyl]biphenyl-2-carbonitrile (0.5 g) in methylene chloride was added to the reaction mixture, and the mixture was further stirred at room temperature for 3 hr. Saturated aqueous ammonium chloride solution was added to the reaction mixture, and the mixture was extracted with ethyl acetate. The obtained ethyl acetate layer was washed with saturated brine, and dried over anhydrous magnesium sulfate. The solvent was evaporated under reduced pressure. The obtained residue was purified by silica gel column chromatography to give the title compound as a colorless solid (0.26 g, 52%).

Workup

  1. stirringthe mixture was further stirred at room temperature for 3 hr
  2. extractionthe mixture was extracted with ethyl acetate
  3. washThe obtained ethyl acetate layer was washed with saturated brine
  4. dry with materialdried over anhydrous magnesium sulfate
  5. customThe solvent was evaporated under reduced pressure
  6. customThe obtained residue was purified by silica gel column chromatography

Sources & evidence

ORD record
ord-70c0aeceb6824a0cbe4f7ed79c5481fc
Source dataset
uspto-grants-2014_12
Patent number
US08921379B2

Reaction notes

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