Boron tribromide → HCID 66782170, compound

HRID 1095751Notes

Reaction equation

HRID 1095751 reaction equation
[F:1][CH:2]1[CH:7]([O:8][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[C:16]([C:19]2[N:23]4[CH:24]=[CH:25][C:26]([O:28][CH2:29][CH2:30][O:31]C)=[CH:27][C:22]4=[N:21][CH:20]=2)[CH:15]=[CH:14]3)[CH2:6][CH2:5][NH:4][CH2:3]1.B(Br)(Br)Br>C(Cl)Cl>[F:1][C@H:2]1[C@H:7]([O:8][C:9]2[CH:10]=[CH:11][CH:12]=[C:13]3[C:18]=2[N:17]=[C:16]([C:19]2[N:23]4[CH:24]=[CH:25][C:26]([O:28][CH2:29][CH2:30][OH:31])=[CH:27][C:22]4=[N:21][CH:20]=2)[CH:15]=[CH:14]3)[CH2:6][CH2:5][NH:4][CH2:3]1

Participants

4

Reactant 2

HCID 25134Boron tribromideHCID 66781376HCID 66781376, compound

Product 1

HCID 66782170HCID 66782170, compoundYield 25.4%

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Conditions

Temperature
-78 °C

Procedure

To a flask containing 8-(-3-fluoropiperidin-4-yloxy)-2-(7-(2-methoxyethoxy)imidazo[1,2-a]pyridin-3-yl)quinoline (Prepared according to Example 20; 0.062 g, 0.14 mmol) was added CH2Cl2 (14 mL) and the solution was cooled to −78° C. BBr3 (1.0M in CH2Cl2, 0.71 ml, 0.71 mmol) was added dropwise and the reaction stirred at −78° C. for 1 hour, then slowly warmed to 0° C. over 2.0 hours, then warmed to ambient temperature and stirred for 0.5 hours. The reaction was quenched by the addition of a saturated aqueous NaHCO3 solution (15 mL) and the layers were separated. The aqueous phase was extracted with CH2Cl2 and the combined organic phases were washed with brine and dried over Na2SO4. The mixture was filtered and concentrated in vacuo and purified via column chromatography (6% NH4OH in MeOH/CH2Cl2, 2% to 20% linear gradient) to afford 0.015 g (0.25%) of the title compound as a solid. MS APCI (+) m/z 423.2 [M+H]+ detected.

Workup

  1. temperatureslowly warmed to 0° C. over 2.0 hours
  2. temperaturewarmed to ambient temperature
  3. stirringstirred for 0.5 hours
  4. customThe reaction was quenched by the addition of a saturated aqueous NaHCO3 solution (15 mL)
  5. customthe layers were separated
  6. extractionThe aqueous phase was extracted with CH2Cl2
  7. washthe combined organic phases were washed with brine
  8. dry with materialdried over Na2SO4
  9. filtrationThe mixture was filtered
  10. concentrationconcentrated in vacuo
  11. custompurified via column chromatography (6% NH4OH in MeOH/CH2Cl2, 2% to 20% linear gradient)

Sources & evidence

ORD record
ord-461915d79ddf482ca857c8039679768c
Source dataset
uspto-grants-2012_03
Patent number
US08138181B2

Reaction notes

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