Sodium Bicarbonate → HCID 57417126, compound

HRID 552558Notes

Reaction equation

HRID 552558 reaction equation
[C:1]([C:3]1[N:8]=[CH:7][C:6]([C:9](OC)=[O:10])=[C:5]([C:13](OC)=[O:14])[CH:4]=1)#[N:2].[BH4-].[Li+].C([O-])(O)=O.[Na+]>CCO.C1COCC1>[OH:14][CH2:13][C:5]1[C:6]([CH2:9][OH:10])=[CH:7][N:8]=[C:3]([C:1]#[N:2])[CH:4]=1

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 15813712HCID 15813712, compound2×

Product 1

HCID 57417126HCID 57417126, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 6-cyanopyridine-3,4-dicarboxylate (2.00 g, 9.08 mmol) [Hashimoto et al. (1997) Heterocycles 46, 581] in EtOH (50 mL) was added lithium borohydride (4.54 mL of a 2 M solution in THF, 9.08 mmol) dropwise. The reaction mixture was stirred at ambient temperature for 3 h, and then cooled to 0° C. Saturated aqueous NaHCO3 (20 mL) was added slowly and the quenched mixture was extracted with EtOAc (9×100 mL). The combined organic extracts were dried over Na2SO4, filtered, and concentrated in vacuo. The crude product was purified by silica gel chromatography, eluting with a gradient of CH2Cl2:MeOH-100:0 to 85:15, to give the title compound. MS: m/z=165 (M+1).

Workup

  1. temperaturecooled to 0° C
  2. extractionthe quenched mixture was extracted with EtOAc (9×100 mL)
  3. dry with materialThe combined organic extracts were dried over Na2SO4
  4. filtrationfiltered
  5. concentrationconcentrated in vacuo
  6. customThe crude product was purified by silica gel chromatography
  7. washeluting with a gradient of CH2Cl2

Sources & evidence

ORD record
ord-ce16b0c3b0cb45a19a6b7af9ecf4fb9d
Source dataset
uspto-grants-2011_05
Patent number
US07951795B2

Reaction notes

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