Phosphate → HCID 23434113, compound

HRID 2121728Notes

Reaction equation

HRID 2121728 reaction equation
[N:1]1[CH:6]=[CH:5][C:4]([C:7]2[S:8][C:9]([C:15]3[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=3)=[C:10]([CH3:14])[C:11]=2[CH:12]=[O:13])=[CH:3][CH:2]=1.[BH4-].[Na+].P([O-])([O-])([O-])=O>CO>[OH:13][CH2:12][C:11]1[C:10]([CH3:14])=[C:9]([C:15]2[CH:20]=[CH:19][N:18]=[CH:17][CH:16]=2)[S:8][C:7]=1[C:4]1[CH:5]=[CH:6][N:1]=[CH:2][CH:3]=1

Participants

5

Reactant 3

HCID 1061PhosphateHCID 4311764Sodium borohydrideHCID 121127812,5-Di(4-pyridyl)-4-methylthiophene-3-carbaldehyde

Product 1

HCID 23434113HCID 23434113, compoundYield 116.4%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent2×

Procedure

To a stirred solution of 2,5-di(4-pyridyl)-4-methylthiophene-3-carbaldehyde (0.145 g) in methanol (10 mL) was added sodium borohydride (0.11 g) at 0° C. The mixture was stirred at room temperature for 30 minutes. Phosphate buffer was added to the reaction mixture and MeOH was removed by evaporation. The residue was extracted with ethyl acetate (30 mL×2). The combined organic layers were washed with brine, dried over MgSO4, and concentrated in vacuo. The resulting residue was purified by flash chromatography eluting with ethyl acetate-CH2Cl2-MeOH (1:1:0.04) to give the subtitle compound (0.170 g).

Workup

  1. customwas removed by evaporation
  2. extractionThe residue was extracted with ethyl acetate (30 mL×2)
  3. washThe combined organic layers were washed with brine
  4. dry with materialdried over MgSO4
  5. concentrationconcentrated in vacuo
  6. customThe resulting residue was purified by flash chromatography
  7. washeluting with ethyl acetate-CH2Cl2-MeOH (1:1:0.04)

Sources & evidence

ORD record
ord-019ceffdb2c345b582fd5c5866853ce5
Source dataset
uspto-grants-2004_02
Patent number
US06696470B2

Reaction notes

Loading…