Boron tribromide → HCID 66813165, compound

HRID 333828Notes

Reaction equation

HRID 333828 reaction equation
[CH2:1]([O:3][C:4]([CH:6]1[CH2:11][CH2:10][N:9]([C:12]2[CH:17]=[C:16]([C:18]([OH:34])([C:30]([F:33])([F:32])[F:31])[CH:19]([C:21]3[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][C:22]=3[Cl:29])[CH3:20])[CH:15]=[CH:14][N:13]=2)[CH2:8][CH2:7]1)=[O:5])[CH3:2].B(Br)(Br)Br>ClCCl>[CH2:1]([O:3][C:4]([CH:6]1[CH2:7][CH2:8][N:9]([C:12]2[CH:17]=[C:16]([C:18]([OH:34])([C:30]([F:31])([F:32])[F:33])[CH:19]([C:21]3[CH:26]=[CH:25][C:24]([OH:27])=[CH:23][C:22]=3[Cl:29])[CH3:20])[CH:15]=[CH:14][N:13]=2)[CH2:10][CH2:11]1)=[O:5])[CH3:2]

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 25254609HCID 25254609, compound

Product 1

HCID 66813165HCID 66813165, compoundYield 74%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent2×

Procedure

4′-[2-(2-Chloro-4-methoxy-phenyl)-1-hydroxy-1-trifluoromethyl-propyl]-3,4,5,6-tetrahydro-2H-[1,2′]bipyridinyl-4-carboxylic acid ethyl ester (Example 154, 57 mg) in dichloromethane (0.5 mL) under argon, was treated with 1M-BBr3 in dichloromethane (0.341 mL). The solution was poured into ice-water/NaHCO3, extracted twice with dichloromethane. The combined organic phases were washed with brine, dried over MgSO4 and evaporated in vacuo. The residue was purified by flash chromatography (4 g silica gel, heptane/ethyl acetate 2/1) to give the title compound as amorphous colorless solid (41 mg). MS (m/e)=487.2 (MH+).

Workup

  1. extractionextracted twice with dichloromethane
  2. washThe combined organic phases were washed with brine
  3. dry with materialdried over MgSO4
  4. customevaporated in vacuo
  5. customThe residue was purified by flash chromatography (4 g silica gel, heptane/ethyl acetate 2/1)

Sources & evidence

ORD record
ord-a0f2fb6a0f9a485e97f8ed862f699ee4
Source dataset
uspto-grants-2014_11
Patent number
US08883786B2

Reaction notes

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