4-Pyridinecarboxaldehyde → HCID 11474626, compound

HRID 2251875Notes

Reaction equation

HRID 2251875 reaction equation
[NH2:1][C:2]1[CH:10]=[CH:9][CH:8]=[C:7]2[C:3]=1[C:4](=[O:22])[N:5]([C:12]1[CH:17]=[CH:16][C:15]([C:18]([CH3:21])([CH3:20])[CH3:19])=[CH:14][CH:13]=1)[C:6]2=[O:11].[N:23]1[CH:28]=[CH:27][C:26]([CH:29]=O)=[CH:25][CH:24]=1.[BH-](OC(C)=O)(OC(C)=O)OC(C)=O.[Na+]>ClCCCl>[C:18]([C:15]1[CH:16]=[CH:17][C:12]([N:5]2[C:4](=[O:22])[C:3]3[C:7](=[CH:8][CH:9]=[CH:10][C:2]=3[NH:1][CH2:29][C:26]3[CH:27]=[CH:28][N:23]=[CH:24][CH:25]=3)[C:6]2=[O:11])=[CH:13][CH:14]=1)([CH3:19])([CH3:21])[CH3:20]

Participants

5

Reactant 3

HCID 133894-PyridinecarboxaldehydeHCID 5049666Sodium triacetoxyborohydrideHCID 69032420HCID 69032420, compound

Product 1

HCID 11474626HCID 11474626, compound

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Procedure

In a 25 mL round bottomed flask, 4-amino-2-(4-tert-butyl-phenyl)-isoindole-1,3-dione (30 mg, 0.101 mmol, Step B) was dissolved in 1,2-dichloroethane (10 mL). To this was added 4-pyridinecarboxaldehyde (0.05 mL, 0.524 mmol). The reaction was stirred for 1 h under N2. NaBH(OAc)3 (40 mg, 0.188 mmol) was added and the suspension was stirred for 6 h. The reaction was quenched with saturated NaHCO3 solution (50 mL). The reaction was rotary evaporated to remove the 1,2-dichloroethane. The product was extracted with EtOAc (3×50 mL). The combined organics were washed with brine (50 mL), dried over Na2SO4, filtered and concentrated to afford an oil. The oil was purified by flash chromatography on silica gel eluting with 30% EtOAc in hexanes. MS (ES+): 386.1 (M+H)+. Calc'd for C24H23N3O2-385.46.

Workup

  1. stirringthe suspension was stirred for 6 h
  2. customThe reaction was quenched with saturated NaHCO3 solution (50 mL)
  3. customThe reaction was rotary evaporated
  4. customto remove the 1,2-dichloroethane
  5. extractionThe product was extracted with EtOAc (3×50 mL)
  6. washThe combined organics were washed with brine (50 mL)
  7. dry with materialdried over Na2SO4
  8. filtrationfiltered
  9. concentrationconcentrated
  10. customto afford an oil
  11. customThe oil was purified by flash chromatography on silica gel eluting with 30% EtOAc in hexanes

Sources & evidence

ORD record
ord-b75fa90ff8c94f5e9971cbb0ad8eaeea
Source dataset
uspto-grants-2008_01
Patent number
US07320992B2

Reaction notes

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