Isobutanol → HCID 66659202, compound

HRID 420537Notes

Reaction equation

HRID 420537 reaction equation
[H-].[Na+].[CH3:3][CH:4]([CH3:7])[CH2:5][OH:6].[Br:8][C:9]1[N:13]2[CH:14]=[C:15]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])[C:16]([C:19]#[N:20])=[C:17](Cl)[C:12]2=[N:11][CH:10]=1>O>[Br:8][C:9]1[N:13]2[CH:14]=[C:15]([C:21]3[CH:26]=[CH:25][C:24]([Cl:27])=[CH:23][C:22]=3[Cl:28])[C:16]([C:19]#[N:20])=[C:17]([O:6][CH2:5][CH:4]([CH3:7])[CH3:3])[C:12]2=[N:11][CH:10]=1

Participants

5

Reactant 3

HCID 6560IsobutanolHCID 24758Sodium hydrideHCID 66659003HCID 66659003, compound

Product 1

HCID 66659202HCID 66659202, compoundYield 63%

Reagents, catalysts & solvents 1

HCID 962WaterSolvent

Conditions

Temperature
70 °C

Procedure

NaH (60% in mineral oil, 149 mg, 3.7 mmol) was carefully added to 2-methyl-1-propanol (10 mL) at 0° C. (ice bath). The mixture was stirred at RT for 10 min before 3-bromo-8-chloro-6-(2,4-dichloro-phenyl)-imidazo[1,2-a]pyridine-7-carbonitrile (500 mg, 1.25 mmol) was added in one portion. The reaction mixture was heated at 70° C. and stirred for 1 h, then cooled to RT and poured into water (100 mL). The formed slurry was extracted successively with DCM (2×50 mL) and AcOEt (50 mL), and the combined organic fractions were dried over Na2SO41 filtered, and evaporated to dryness. The remaining residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, hexane/TBME 95.5→100% TBME) to yield the title compound (348 mg, 0.79 mmol, 63%). MS: 438 [M+1]+; HPLC: AtRet=3.36; TLC: RF 0.81 (hexane/TBME 1:1).

Workup

  1. additionwas added in one portion
  2. temperaturecooled to RT
  3. extractionThe formed slurry was extracted successively with DCM (2×50 mL) and AcOEt (50 mL)
  4. customthe combined organic fractions were dried over Na2SO41
  5. filtrationfiltered
  6. customevaporated to dryness
  7. customThe remaining residue was purified by Combi-Flash Companion™ (Isco Inc.) column chromatography (SiO2; gradient elution, hexane/TBME 95.5→100% TBME)

Sources & evidence

ORD record
ord-441df234b5b74b2eb4d0789b640f1c6d
Source dataset
uspto-grants-2012_01
Patent number
US08097617B2

Reaction notes

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