Boron tribromide → N-(5-bicyclo[2.2.1]heptanyl-methyl)-2-[3-(4-hydroxy-phenyl)-propylsulfanyl]-pyridine-3-carboxylic acid amide

HRID 2044168Notes

Reaction equation

HRID 2044168 reaction equation
[CH:1]12[CH2:29][CH:4]([CH:5]([CH2:7][NH:8][C:9]([C:11]3[C:12]([S:17][CH2:18][CH2:19][CH2:20][C:21]4[CH:26]=[CH:25][C:24]([O:27]C)=[CH:23][CH:22]=4)=[N:13][CH:14]=[CH:15][CH:16]=3)=[O:10])[CH2:6]1)[CH2:3][CH2:2]2.B(Br)(Br)Br>C(Cl)Cl>[CH:1]12[CH2:29][CH:4]([CH:5]([CH2:7][NH:8][C:9]([C:11]3[C:12]([S:17][CH2:18][CH2:19][CH2:20][C:21]4[CH:22]=[CH:23][C:24]([OH:27])=[CH:25][CH:26]=4)=[N:13][CH:14]=[CH:15][CH:16]=3)=[O:10])[CH2:6]1)[CH2:3][CH2:2]2

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 46909518HCID 46909518, compound2×

Product 1

HCID 46908911N-(5-bicyclo[2.2.1]heptanyl-methyl)-2-[3-(4-hydroxy-phenyl)-propylsulfanyl]-pyridine-3-carboxylic acid amideYield 84%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

A solution of 483 mg (1.18 mmol) of N-(5-bicyclo[2.2.1]heptanyl-methyl)-2-[3-(4-methoxyphenyl)-propylsulfanyl]-pyridine-3-carboxylic acid amide (exemplary compound 56) in DCM (50 ml) was cooled to −60° C.; 11.8 ml (11.8 mmol, 1M in DCM) of boron tribromide were added at that temperature and stirring was carried out for 90 min at −60° C. After warming to RT, the mixture was quenched with a 1M aq. NaHCO3 sol. and the phases were separated. The aqueous phase was extracted with EA and the organic phases were combined, washed with water, dried over MgSO4, filtered and concentrated in vacuo. Crystallization (hexane/EA 2:1) of the residue yielded 393 mg (0.99 mmol, 84%) of N-(5-bicyclo[2.2.1]heptanyl-methyl)-2-[3-(4-hydroxy-phenyl)-propylsulfanyl]-pyridine-3-carboxylic acid amide. MS: m/z 397.2 [M+H]+.

Workup

  1. customthe mixture was quenched with a 1M aq. NaHCO3 sol.
  2. customthe phases were separated
  3. extractionThe aqueous phase was extracted with EA
  4. washwashed with water
  5. dry with materialdried over MgSO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customCrystallization (hexane/EA 2:1) of the residue

Sources & evidence

ORD record
ord-b99825c8202442c79f1200df750c7499
Source dataset
uspto-grants-2013_11
Patent number
US08586755B2

Reaction notes

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