Boron tribromide → [5-(2-Hydroxy-pyrimidin-5-yl)-3-methyl-2-(4-trifluoromethyl-phenyl)-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

HRID 545448Notes

Reaction equation

HRID 545448 reaction equation
C[O:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:23])([F:22])[F:21])=[CH:16][CH:15]=3)[N:11]([CH3:24])[C:10]=2[C:25]([N:27]2[CH2:32][CH2:31][CH:30]([N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)[CH2:29][CH2:28]2)=[O:26])=[CH:5][N:4]=1.B(Br)(Br)Br.C(=O)([O-])O.[Na+]>C(Cl)Cl>[OH:2][C:3]1[N:8]=[CH:7][C:6]([C:9]2[N:13]=[C:12]([C:14]3[CH:19]=[CH:18][C:17]([C:20]([F:22])([F:21])[F:23])=[CH:16][CH:15]=3)[N:11]([CH3:24])[C:10]=2[C:25]([N:27]2[CH2:28][CH2:29][CH:30]([N:33]3[CH2:37][CH2:36][CH2:35][CH2:34]3)[CH2:31][CH2:32]2)=[O:26])=[CH:5][N:4]=1

Participants

5

Reactant 3

HCID 25134Boron tribromideHCID 516892Sodium BicarbonateHCID 57541105[5-(2-Methoxy-pyrimidin-5-yl)-3-methyl-2-(4-trifluoromethyl-phenyl)-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone

Product 1

HCID 178479936[5-(2-Hydroxy-pyrimidin-5-yl)-3-methyl-2-(4-trifluoromethyl-phenyl)-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanoneYield 37%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 0.25 g (0.49 mmol) of [5-(2-methoxy-pyrimidin-5-yl)-3-methyl-2-(4-trifluoromethyl-phenyl)-3H-imidazol-4-yl]-(4-pyrrolidin-1-yl-piperidin-1-yl)-methanone (example 114) in 10 ml of MeCl2 was cooled down to 0° C.; then, 0.97 ml (1.0 mMol) of a boron tribromide solution (1.0 molar in MeCl2) were added and the reaction mixture was warmed up to RT. After 3 hours, it was poured into crashed ice, neutralized with an aqueous sodium hydrogen carbonate solution, then extracted twice with MeCl2; the organic phases were washed with water, dried over magnesium sulfate, filtered and evaporated to give 0.089 g (37%) of the title compound as yellow solid. MS: 501.2 (MH+).

Workup

  1. additionit was poured
  2. extractionextracted twice with MeCl2
  3. washthe organic phases were washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. customevaporated

Sources & evidence

ORD record
ord-0e97a3f99b39455cbe2179fc3ff82a1f
Source dataset
uspto-grants-2011_05
Patent number
US07935707B2

Reaction notes

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