Ammonium formate → HCID 67142902, compound

HRID 448674Notes

Reaction equation

HRID 448674 reaction equation
[NH2:1][C:2]1[C:3]2[C:10]([C:11]#[N:12])=[C:9](Br)[N:8]([C@@H:14]3[O:22][C@H:21]([CH2:23][O:24][C:25](=[O:32])[C:26]4[CH:31]=[CH:30][CH:29]=[CH:28][CH:27]=4)[C@@H:20]([CH3:33])[C@H:15]3[O:16][C:17](=[O:19])[CH3:18])[C:4]=2[N:5]=[CH:6][N:7]=1.C([O-])=O.[NH4+]>CCO.[Pd]>[NH2:1][C:2]1[C:3]2[C:10]([C:11]#[N:12])=[CH:9][N:8]([C@@H:14]3[O:22][C@H:21]([CH2:23][O:24][C:25](=[O:32])[C:26]4[CH:27]=[CH:28][CH:29]=[CH:30][CH:31]=4)[C@@H:20]([CH3:33])[C@H:15]3[O:16][C:17](=[O:19])[CH3:18])[C:4]=2[N:5]=[CH:6][N:7]=1

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 67142223HCID 67142223, compound

Product 1

HCID 67142902HCID 67142902, compoundYield 68.9%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Procedure

To a suspension of the title compound from Step A (183 mg, 0.35 mmol) in EtOH (9 mL) were added ammonium formate (0.23 g, 3.6 mmol) and 10% palladium on activated carbon (20 mg) and the mixture was heated at reflux for 1.5 h. The hot reaction mixture was filtered through Celite and washed with hot EtOH. The solvent was removed and the residue treated with MeOH. The pale yellow solid was filtered thus yielding 105 mg of pure title compound. The filtrate was evaporated and purified on a silica gel column with a solvent system of CH2Cl2/MeOH: 50/1 to afford an additional 63 mg of title compound as a white solid.

Workup

  1. temperaturethe mixture was heated
  2. temperatureat reflux for 1.5 h
  3. filtrationThe hot reaction mixture was filtered through Celite
  4. washwashed with hot EtOH
  5. customThe solvent was removed
  6. additionthe residue treated with MeOH
  7. filtrationThe pale yellow solid was filtered thus

Sources & evidence

ORD record
ord-a7a9bb1d1ee5465d871856bb1e4c2e93
Source dataset
uspto-grants-2013_07
Patent number
US08481712B2

Reaction notes

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