Sodium Methoxide → HCID 18796931, compound

HRID 442778Notes

Reaction equation

HRID 442778 reaction equation
[NH2:1][C:2]1[C:6]2[C:7](Cl)=[N:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13].[CH3:16][O-:17].[Na+]>CO>[NH2:1][C:2]1[C:6]2[C:7]([O:17][CH3:16])=[N:8][CH:9]=[CH:10][C:5]=2[S:4][C:3]=1[C:12]([O:14][CH3:15])=[O:13]

Participants

4

Reactant 2

HCID 10942334Sodium MethoxideHCID 18796968Methyl 3-amino-4-chlorothieno[3,2-c]pyridine-2-carboxylate

Product 1

HCID 18796931HCID 18796931, compoundYield 94.2%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

The product from Example 48A (1.2 g, 4.9 mmol) and sodium methoxide (1.0 g, 19 mmol) were refluxed in 30 mL MeOH for 6 h. The reaction was partitioned between water and CH2Cl2. The layers were separated and the aqueous layer was extracted with CH2Cl2. The combined organic layers were dried (MgSO4), filtered, and concentrated. Silica gel chromatography (CH2Cl2) yielded 1.1 g (78%) of the title compound: 1H NMR (300 MHz, DMSO-d6) δ 3.79 (s, 3H), 4.05 (s, 3H), 6.96 (bs, 2H), 7.47 (d, J=6 Hz, 1H), 8.07 (d, J=6 Hz, 1H); MS (DCI(NH3)) m/e 239 (M+H)+.

Workup

  1. customThe reaction was partitioned between water and CH2Cl2
  2. customThe layers were separated
  3. extractionthe aqueous layer was extracted with CH2Cl2
  4. dry with materialThe combined organic layers were dried (MgSO4)
  5. filtrationfiltered
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-a0ace30d26874e62a2b837f9dc5f6fb4
Source dataset
uspto-grants-1999_04
Patent number
US05891882

Reaction notes

Loading…