Ammonium formate → 3-(Benzyloxy)-5-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)benzamide

HRID 1011744Notes

Reaction equation

HRID 1011744 reaction equation
[CH3:1][N:2]1[CH:6]=[CH:5][C:4]([NH:7][C:8](=[O:31])[C:9]2[CH:14]=[C:13]([O:15]CC3C=CC=CC=3)[CH:12]=[C:11]([O:23][CH2:24][C:25]3[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=3)[CH:10]=2)=[N:3]1.C([O-])=O.[NH4+]>C(O)C.[Pd]>[OH:15][C:13]1[CH:14]=[C:9]([CH:10]=[C:11]([O:23][CH2:24][C:25]2[CH:30]=[CH:29][CH:28]=[CH:27][CH:26]=2)[CH:12]=1)[C:8]([NH:7][C:4]1[CH:5]=[CH:6][N:2]([CH3:1])[N:3]=1)=[O:31]

Participants

5

Reactant 2

HCID 2723923Ammonium formateHCID 53629651N-(1-methyl-1H-pyrazol-3-yl)-3,5-bis[(phenylmethyl)oxy]benzamide

Product 1

HCID 591271193-(Benzyloxy)-5-hydroxy-N-(1-methyl-1H-pyrazol-3-yl)benzamideYield 48.3%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 702EthanolSolvent

Conditions

Temperature
140 °C

Procedure

A suspension of N-(1-methyl-1H-pyrazol-3-yl)-3,5-bis[(phenylmethyl)oxy]benzamide (1.0 g, 2.42 mmol) was dissolved in ethanol (12 mL) and ammonium formate (229 mg, 3.63 mmol) was added in one portion. The reaction was blanketed with argon and 10% palladium on activated carbon (10 mg) was added. This mixture was heated to 140° C. for 5 minutes in a Smith Creator microwave. The catalyst was filtered off and the volatiles removed in vacuo, the residue was chromatographed on silica, eluting with a gradient of 30-100% ethyl acetate in iso-hexane, to give the title compound as a white solid (378 mg).

Workup

  1. additionwas added
  2. filtrationThe catalyst was filtered off
  3. customthe volatiles removed in vacuo
  4. customthe residue was chromatographed on silica
  5. washeluting with a gradient of 30-100% ethyl acetate in iso-hexane

Sources & evidence

ORD record
ord-8b0fd3442ba8484f948b32b16c9879a4
Source dataset
uspto-grants-2011_07
Patent number
US07977328B2

Reaction notes

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