Acetic Acid → HCID 22563227, compound

HRID 982712Notes

Reaction equation

HRID 982712 reaction equation
[CH:1]([C:3]1[S:11][C:10]2[C:9](=[O:12])[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][NH:6][C:5]=2[CH:4]=1)=[O:2].C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+].C(=O)(O)[O-].[Na+]>ClCCCl.C(Cl)Cl>[OH:2][CH2:1][C:3]1[S:11][C:10]2[C:9](=[O:12])[C:8]([C:13]([O:15][CH2:16][CH3:17])=[O:14])=[CH:7][NH:6][C:5]=2[CH:4]=1

Participants

7

Reactant 4

HCID 176Acetic AcidHCID 516892Sodium BicarbonateHCID 5049666Sodium triacetoxyborohydrideHCID 22563214HCID 22563214, compound

Product 1

HCID 22563227HCID 22563227, compoundYield 76.8%

Reagents, catalysts & solvents 2

HCID 111,2-DichloroethaneSolventHCID 6344DichloromethaneSolvent

Conditions

Temperature
0 °C

Procedure

To a 0° C. mixture of ethyl 2-formyl-7-oxo-4,7-dihydrothieno[3,2-b]pyridine-6-carboxylate (Preparation 6, 0.628 g, 2.5 mmol) and acetic acid (0.71 mL, 12.5 mmol) in 1,2-dichloroethane (23 mL) was added sodium triacetoxyborohydride (1.06 g, 5.0 mmol). The mixture was stirred at 0° C. for 5 minutes and at room temperature for 24 hrs. A saturated solution of sodium bicarbonate (25 mL) and methylene chloride (25 mL) were added. After stirring vigorously for 5 minutes, the mixture was filtered. The collected solid was washed with water and methylene chloride, then dried in vacuo, leaving the title compound as a pale yellow solid (0.486 g).

Workup

  1. stirringAfter stirring vigorously for 5 minutes
  2. filtrationthe mixture was filtered
  3. washThe collected solid was washed with water and methylene chloride
  4. customdried in vacuo

Sources & evidence

ORD record
ord-cef5cf4fc3d2498db4f4249f85bc922f
Source dataset
uspto-grants-2005_03
Patent number
US06861438B2

Reaction notes

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