Phosphate → HCID 23434113, compound

HRID 1004178Notes

Reaction equation

HRID 1004178 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

Sources & evidence

ORD record
ord-86a255cc51c648599cbc3f47bfdc02b0
Source dataset
uspto-grants-2000_04
Patent number
US06048880

Reaction notes

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