Water → Methyl thieno(3,2-b)pyridine-2-carboxylate

HRID 1890509Notes

Reaction equation

HRID 1890509 reaction equation
N[C:2]1[C:6]2=[N:7][CH:8]=[CH:9][CH:10]=[C:5]2[S:4][C:3]=1[C:11]([O:13][CH3:14])=[O:12].N([O-])=O.[Na+].O.[OH-].[Na+]>[PH2](O)=O>[S:4]1[C:5]2[C:6](=[N:7][CH:8]=[CH:9][CH:10]=2)[CH:2]=[C:3]1[C:11]([O:13][CH3:14])=[O:12]

Participants

6

Reactant 4

HCID 962WaterHCID 14798Sodium HydroxideHCID 13793447Methyl 3-aminothieno[3,2-b]pyridine-2-carboxylateHCID 23668193Sodium Nitrite

Product 1

HCID 22047416Methyl thieno(3,2-b)pyridine-2-carboxylate

Reagents, catalysts & solvents 1

HCID 4124402Phosphinic AcidSolvent

Procedure

To a solution of methyl 3-aminothieno[3,2-b]pyridine-2-carboxylate (C-2) (930 mg, 4.47 mmol) in hypophosphorous acid (35 mL) chilled in an ice bath was added sodium nitrite (620 mg, 8.98 mmol) in a minimal amount of water. The reaction mixture was stirred for 3 h in an ice bath, and then the pH was adjusted to about 7.0 with 30% aqueous sodium hydroxide solution. The resulting mixture was extracted with EtOAc. The combined organic layers were dried and concentrated to afford the title compound. MS (m/z): 194 (M+1)+.

Workup

  1. extractionThe resulting mixture was extracted with EtOAc
  2. customThe combined organic layers were dried
  3. concentrationconcentrated

Sources & evidence

ORD record
ord-a16368c705224c03afce43d0d30b0bc1
Source dataset
uspto-grants-2013_08
Patent number
US08507487B2

Reaction notes

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