Toluene → HCID 21717324, compound

HRID 1386062Notes

Reaction equation

HRID 1386062 reaction equation
[CH3:1]OCCO[AlH2-]OCCOC.[Na+].[C:13]([C:18]1[N:22]2[CH:23]=[CH:24][CH:25]=[C:26]([NH:27][C:28](C)(C)C3C=CC=CC=3)[C:21]2=[N:20][C:19]=1[CH3:37])(OCC)=[O:14].[C:38]1([CH3:44])[CH:43]=[CH:42][CH:41]=[CH:40][CH:39]=1>>[CH3:44][C:38]1[CH:43]=[CH:42][CH:41]=[C:40]([CH3:1])[C:39]=1[CH2:28][NH:27][C:26]1[C:21]2[N:22]([C:18]([CH2:13][OH:14])=[C:19]([CH3:37])[N:20]=2)[CH:23]=[CH:24][CH:25]=1

Participants

4

Reactant 3

HCID 1140Toluene2×HCID 16684438Red-AlHCID 131722785HCID 131722785, compound

Product 1

HCID 21717324HCID 21717324, compound

Procedure

A solution of vitride (40 ml, 136 mmol) in toluene (25 ml) was added dropwise to a nitrogen-purged solution of 3-carboethoxy-8-(dimethylbenzylamino)-2-methylimidazo[1,2-a]pyridine (8.0 g, 23.71 mmol) in toluene (100 ml). The ice-bath was removed and the reaction mixture was stirred at room temperature for 105 min. The reaction mixture was cooled to 0° C. and quenched by addition of water (36 ml). The mixture was filtered and the organic layer washed with aqueous NaHCO3, dried over Na2SO4 and concentrated. Acetonitrile (20 ml) was added and the product was collected by filtration. The crystalline product was washed twice with acetonitrile and dried in vacuo. Yield 5.6 g.

Workup

  1. customThe ice-bath was removed
  2. temperatureThe reaction mixture was cooled to 0° C.
  3. customquenched by addition of water (36 ml)
  4. filtrationThe mixture was filtered
  5. washthe organic layer washed with aqueous NaHCO3
  6. dry with materialdried over Na2SO4
  7. concentrationconcentrated
  8. additionAcetonitrile (20 ml) was added
  9. filtrationthe product was collected by filtration
  10. washThe crystalline product was washed twice with acetonitrile
  11. customdried in vacuo

Sources & evidence

ORD record
ord-8657cbc1dace4f66bca278dee2f26560
Source dataset
uspto-grants-2001_07
Patent number
US06265415B1

Reaction notes

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