2-(4-{1-azido-2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]ethyl}phenyl)-5-fluoropyridine → 2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanamine

HRID 216381Notes

Reaction equation

HRID 216381 reaction equation
[N:1]([CH:4]([C:36]1[CH:41]=[CH:40][C:39]([C:42]2[CH:47]=[CH:46][C:45]([F:48])=[CH:44][N:43]=2)=[CH:38][CH:37]=1)[CH2:5][C:6]1[N:7]([C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)[C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[CH:8]=[C:9]([CH2:11][C:12]([CH3:16])([CH3:15])[CH2:13][CH3:14])[N:10]=1)=[N+]=[N-]>CO.[Pd]>[CH3:15][C:12]([CH3:16])([CH2:13][CH3:14])[CH2:11][C:9]1[N:10]=[C:6]([CH2:5][CH:4]([C:36]2[CH:37]=[CH:38][C:39]([C:42]3[CH:47]=[CH:46][C:45]([F:48])=[CH:44][N:43]=3)=[CH:40][CH:41]=2)[NH2:1])[N:7]([C:17]([C:30]2[CH:35]=[CH:34][CH:33]=[CH:32][CH:31]=2)([C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)[C:24]2[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=2)[CH:8]=1

Participants

4

Reactant 1

HCID 866385012-(4-{1-azido-2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]ethyl}phenyl)-5-fluoropyridine

Product 1

HCID 686682132-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanamine

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 887MethanolSolvent

Procedure

Pd (10 wt % on activated carbon) (10 mg, cat.) was added to a degassed solution of 2-(4-{1-azido-2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]ethyl}phenyl)-5-fluoropyridine (110 mg, 0.17 mmol) in methanol (6 mL). After stirring under an atmosphere of hydrogen overnight, the reaction mixture was filtered through celite rinsing with methanol. The filtrate was concentrated to afford 2-[4-(2,2-dimethylbutyl)-1-trityl-1H-imidazol-2-yl]-1-[4-(5-fluoropyridin-2-yl)phenyl]ethanamine which was used in the next step without further purification.

Workup

  1. filtrationthe reaction mixture was filtered
  2. washthrough celite rinsing with methanol
  3. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-47b594fa4005452fa800752858d725c3
Source dataset
uspto-grants-2012_06
Patent number
US08193228B2

Reaction notes

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