Ammonium formate → HCID 68630751, compound

HRID 1847262Notes

Reaction equation

HRID 1847262 reaction equation
[CH2:1]([O:5][C:6]([C:8]1[N:13]=[C:12](Br)[C:11]2[C:15]([CH3:18])=[N:16][S:17][C:10]=2[C:9]=1[OH:19])=[O:7])[CH2:2][CH2:3][CH3:4].C([O-])=O.[NH4+]>[Pd].CCO.CCOC(C)=O>[CH2:1]([O:5][C:6]([C:8]1[N:13]=[CH:12][C:11]2[C:15]([CH3:18])=[N:16][S:17][C:10]=2[C:9]=1[OH:19])=[O:7])[CH2:2][CH2:3][CH3:4]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 86649354HCID 86649354, compound

Product 1

HCID 68630751HCID 68630751, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 21584252Ethanol ethylacetateSolvent

Procedure

A mixture of 4-Bromo-7-hydroxy-3-methyl-isothiazolo[4,5-c]pyridine-6-carboxylic acid butyl ester (0.19 mmol), 10% Pd/C (33 mg), ammonium formate (9.7 mmol), and EtOH/EtOAc (1:1, 1.9 mL) was refluxed with stirring for 4 h. After cooling to r.t. the mixture was filtered and the filtrate was concentrated in vacuo. The residue was purified by flash column chromatography on silica gel. Eluting with 0-20% EtOAc/CH2Cl2 gave the title compound (35.4 mg) as a white solid: MS (m/z) 267.2 (M+1).

Workup

  1. temperaturewas refluxed
  2. filtrationwas filtered
  3. concentrationthe filtrate was concentrated in vacuo
  4. customThe residue was purified by flash column chromatography on silica gel
  5. washEluting with 0-20% EtOAc/CH2Cl2

Sources & evidence

ORD record
ord-b0d6183c47b3461685507e2e892168f8
Source dataset
uspto-grants-2015_02
Patent number
US08952160B2

Reaction notes

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