Hydrochloric Acid → C-[3-bromo-6-(2,4-dichloro-phenyl)-8-isobutoxy-imidazo[1,2-a]pyridin-7-yl]-methylamine

HRID 420542Notes

Reaction equation

HRID 420542 reaction equation
[Br:1][C:2]1[N:6]2[CH:7]=[C:8]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[C:9]([C:16]#[N:17])=[C:10]([O:11][CH2:12][CH:13]([CH3:15])[CH3:14])[C:5]2=[N:4][CH:3]=1.B.C1COCC1.Cl>C1COCC1.O1CCOCC1>[Br:1][C:2]1[N:6]2[CH:7]=[C:8]([C:18]3[CH:23]=[CH:22][C:21]([Cl:24])=[CH:20][C:19]=3[Cl:25])[C:9]([CH2:16][NH2:17])=[C:10]([O:11][CH2:12][CH:13]([CH3:14])[CH3:15])[C:5]2=[N:4][CH:3]=1

Participants

6

Reactant 3

HCID 313Hydrochloric AcidHCID 2723981Borane;tetrahydrofuranHCID 66659202HCID 66659202, compound

Product 1

HCID 66659438C-[3-bromo-6-(2,4-dichloro-phenyl)-8-isobutoxy-imidazo[1,2-a]pyridin-7-yl]-methylamine

Reagents, catalysts & solvents 2

HCID 312751,4-DioxaneCatalystHCID 8028TetrahydrofuranSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of 3-bromo-6-(2,4-dichloro-phenyl)-8-isobutoxy-imidazo[1,2-a]pyridine-7-carbonitrile (477 mg, 1.0 mmol, prepared according to Example 35, Step 20.2) in anhydrous THF (12 mL) were added a BH3.THF complex (1.0 M solution in THF, 4.5 mL, 4.5 mmol) followed by a 4M HCl solution in dioxane (10 drops) at RT. The reaction mixture was heated at 50° C. and stirred for 3 h, then cooled to 0° C. (ice bath), quenched by the cautious addition of a 2M HCl solution in water (10 mL) and poured into water (100 mL). The aqueous mixture was washed with Et2O (2×30 mL) then basified to pH 10 by the addition of a 2M Na2cO3 solution in water and extracted with DCM (2×30 mL). The combined organic fractions were dried over Na2SO4, filtered, and evaporated to dryness to yield the crude C-[3-bromo-6-(2,4-dichloro-phenyl)-8-isobutoxy-imidazo[1,2-a]pyridin-7-yl]-methylamine intermediate.

Workup

  1. temperaturecooled to 0° C. (ice bath)
  2. customquenched by the cautious addition of a 2M HCl solution in water (10 mL)
  3. additionpoured into water (100 mL)
  4. washThe aqueous mixture was washed with Et2O (2×30 mL)
  5. additionthen basified to pH 10 by the addition of a 2M Na2cO3 solution in water
  6. extractionextracted with DCM (2×30 mL)
  7. dry with materialThe combined organic fractions were dried over Na2SO4
  8. filtrationfiltered
  9. customevaporated to dryness

Sources & evidence

ORD record
ord-5eb584a6269e440280ceed51571de2d9
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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