Sodium borohydride → [3,3']bipyridinyl-5-yl-methanol

HRID 353782Notes

Reaction equation

HRID 353782 reaction equation
C([O:3][C:4]([C:6]1[CH:7]=[C:8]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:9]=[N:10][CH:11]=1)=O)C.[BH4-].[Na+]>C(O)C>[N:10]1[CH:11]=[C:6]([CH2:4][OH:3])[CH:7]=[C:8]([C:12]2[CH:13]=[N:14][CH:15]=[CH:16][CH:17]=2)[CH:9]=1

Participants

4

Reactant 2

HCID 4311764Sodium borohydrideHCID 11535941HCID 11535941, compound

Product 1

HCID 11528472[3,3']bipyridinyl-5-yl-methanolYield 34%

Reagents, catalysts & solvents 1

HCID 702EthanolSolvent

Conditions

Temperature
50 °C

Procedure

To a solution of [3,3′]bipyridinyl-5-carboxylic acid ethyl ester (1 eq) in ethanol was added sodium borohydride (2 eq) at room temperature. The reaction mixture was heated in a 50° C. oil bath for 60 minutes and then quenched by addition of H2O. Once the reaction solvent was removed in vacuo, a solution of the residue in dichloromethane was washed with NaCl(sat), dried over sodium sulfate, filtered and concentrated. The crude solid was purified by flash chromatography using a solvent gradient of 95% DCM, 5% MeOH and 0.1% TEA to yield [3,3′]bipyridinyl-5-yl-methanol (34%). MH+(187).

Workup

  1. customquenched by addition of H2O
  2. customOnce the reaction solvent was removed in vacuo
  3. washa solution of the residue in dichloromethane was washed with NaCl(sat)
  4. dry with materialdried over sodium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated
  7. customThe crude solid was purified by flash chromatography

Sources & evidence

ORD record
ord-c0ba1c77dc444c77aca02363892dad35
Source dataset
uspto-grants-2004_06
Patent number
US06756359B2

Reaction notes

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