Ammonium formate → HCID 68427750, compound

HRID 642321Notes

Reaction equation

HRID 642321 reaction equation
[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:16]=[N:17][CH:18]=[C:19](Br)[CH:20]=3)[S:14][C:8]=2[C:7]=1[OH:22])=[O:5])[CH3:2].C([O-])=O.[NH4+]>C(OCC)(=O)C.[Pd]>[CH2:1]([O:3][C:4]([C:6]1[N:11]=[CH:10][C:9]2[N:12]=[C:13]([C:15]3[CH:16]=[N:17][CH:18]=[CH:19][CH:20]=3)[S:14][C:8]=2[C:7]=1[OH:22])=[O:5])[CH3:2]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 68427372HCID 68427372, compound

Product 1

HCID 68427750HCID 68427750, compoundYield 39%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

A mixture of 2-(5-bromo-pyridin-3-yl)-7-hydroxy-thiazolo[4,5-c]pyridine-6-carboxylic acid ethyl ester (88 mg, 0.23 mmol), ammonium formate (296 mg, 4.63 mmol) and 10% Pd/C (114 mg) in ethyl acetate (7 mL) was refluxed for 21 h before it was cooled to room temperature and filtered. The filtrate was washed with saturated sodium bicarbonate, water, dried and concentrated in vacuo. The residue was purified by flash column chromatography on silica gel with a gradient of methanol and dichloromethane dried in vacuo to give the title compound as a yellow solid (27 mg): MS: (+) m/z 302.07 (M+1); (−) m/z 300.27 (M−1).

Workup

  1. temperaturewas refluxed for 21 h before it
  2. filtrationfiltered
  3. washThe filtrate was washed with saturated sodium bicarbonate, water
  4. customdried
  5. concentrationconcentrated in vacuo
  6. customThe residue was purified by flash column chromatography on silica gel with a gradient of methanol and dichloromethane
  7. customdried in vacuo

Sources & evidence

ORD record
ord-6cf740a2cc82474493bfd4ecd1ff04d5
Source dataset
uspto-grants-2010_04
Patent number
US07696223B2

Reaction notes

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