Lithium borohydride → HCID 70977234, compound

HRID 1521585Notes

Reaction equation

HRID 1521585 reaction equation
[Br:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:15])([CH3:14])[C:9](OCC)=[O:10])[CH:5]=[N:6][CH:7]=1.[BH4-].[Li+]>C(O)C>[Br:1][C:2]1[CH:3]=[C:4]([C:8]([CH3:15])([CH3:14])[CH2:9][OH:10])[CH:5]=[N:6][CH:7]=1

Participants

4

Reactant 2

HCID 4148881Lithium borohydrideHCID 71742853HCID 71742853, compound

Product 1

HCID 70977234HCID 70977234, compound

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Procedure

To a solution of the title compound from Example 53 Step D (93 g, 0.34 mol) in ethanol (1.2 L) was added lithium borohydride (16.6 g, 0.75 mol). The resulting mixture was heated to reflux and stirred overnight. The reaction was then cooled to room temperature and poured onto ice. The mixture was extracted with ethyl acetate, and the organic layer washed with saturated aqueous sodium chloride solution, dried over magnesium sulfate, filtered and concentrated under reduced pressure. Purification by flash chromatograph on silica gel (petroleum ether/ethyl acetate=40/1-8/1) provided the title compound: LCMS m/z 230 [M+H]+; 1H NMR (300 MHz, CDCl3) δ 8.58 (s, 1H), 8.52 (s, 1H), 7.97 (s, 1H), 4.82-4.86 (m, 1H), 3.44-3.46 (m, 2H), 1.24 (s, 6H).

Workup

  1. temperatureThe resulting mixture was heated
  2. temperatureto reflux
  3. additionpoured onto ice
  4. extractionThe mixture was extracted with ethyl acetate
  5. washthe organic layer washed with saturated aqueous sodium chloride solution
  6. dry with materialdried over magnesium sulfate
  7. filtrationfiltered
  8. concentrationconcentrated under reduced pressure
  9. customPurification by flash chromatograph on silica gel (petroleum ether/ethyl acetate=40/1-8/1)

Sources & evidence

ORD record
ord-2a2c3ead515f4c2781ac1de1afc94bb7
Source dataset
uspto-grants-2015_07
Patent number
US09073929B2

Reaction notes

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