Sodium Bicarbonate → HCID 66812945, compound

HRID 1615809Notes

Reaction equation

HRID 1615809 reaction equation
[C:1]([C:3]1[N:8]=[C:7]([C:9](OC)=[O:10])[C:6]([C:13](OC)=[O:14])=[CH:5][CH:4]=1)#[N:2].[BH4-].[Li+].C([O-])(O)=O.[Na+]>CCO.C1COCC1>[OH:14][CH2:13][C:6]1[CH:5]=[CH:4][C:3]([C:1]#[N:2])=[N:8][C:7]=1[CH2:9][OH:10]

Participants

6

Reactant 3

HCID 516892Sodium BicarbonateHCID 4148881Lithium borohydrideHCID 66812986HCID 66812986, compound

Product 1

HCID 66812945HCID 66812945, compound

Reagents, catalysts & solvents 2

HCID 702EthanolSolventHCID 8028TetrahydrofuranSolvent

Procedure

To a solution of dimethyl 6-cyanopyridine-2,3-dicarboxylate from Step A (13.0 g, 59.0 mmol) in EtOH (295 mL) was added lithium borohydride (29.5 mL of a 2 M solution in THF, 59.0 mmol) dropwise. The reaction mixture was stirred at ambient temperature for 4 h, and then cooled to 0° C. Saturated aqueous NaHCO3 (200 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-f1c2f7f9df274c22bbc1713ba8093103
Source dataset
uspto-grants-2014_07
Patent number
US08765759B2

Reaction notes

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