HCID 58293748, compound → HCID 58293830, compound

HRID 446735Notes

Reaction equation

HRID 446735 reaction equation
[C:1]([NH:5][C:6]1[C:11]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([CH:23]=[CH2:24])=[C:19]([F:25])[C:18]=3[F:26])[N:15]=[N:14][N:13]=2)=[CH:10][CH:9]=[CH:8][N:7]=1)([CH3:4])([CH3:3])[CH3:2].[H][H]>C(OCC)(=O)C.[Pd]>[C:1]([NH:5][C:6]1[C:11]([C:12]2[N:16]([C:17]3[CH:22]=[CH:21][C:20]([CH2:23][CH3:24])=[C:19]([F:25])[C:18]=3[F:26])[N:15]=[N:14][N:13]=2)=[CH:10][CH:9]=[CH:8][N:7]=1)([CH3:3])([CH3:2])[CH3:4]

Participants

5

Reactant 2

HCID 58293748HCID 58293748, compound2×HCID 178418361HCID 178418361, compound

Product 1

HCID 58293830HCID 58293830, compoundYield 49.7%

Reagents, catalysts & solvents 2

HCID 23938PalladiumCatalystHCID 8857Ethyl AcetateSolvent

Procedure

N-tert-Butyl-3-(1-(2,3-difluoro-4-vinylphenyl)-1H-tetrazol-5-yl)pyridin-2-amine (Compound 1081, 260 mg) was dissolved in 30 ml of ethyl acetate. 10% Palladium on carbon was added to the mixture and the reaction flask was charged with hydrogen (1 atm). After stirring at RT for 12 hours, the reaction was filtered through diatomaceous earth, concentrated in vacuo, and the residue purified by column chromatography (SiO2), eluting with 0-20% EtOAc/Hexane, to afford 130 mg of N-tert-Butyl-3-(1-(4-ethyl-2,3-difluorophenyl)-1H-tetrazol-5-yl)pyridin-2-amine (Compound 1082); MS (M+1)=359.4.

Workup

  1. filtrationthe reaction was filtered through diatomaceous earth
  2. concentrationconcentrated in vacuo
  3. customthe residue purified by column chromatography (SiO2)
  4. washeluting with 0-20% EtOAc/Hexane

Sources & evidence

ORD record
ord-44b8c1a8c568443482ebc6a438389a23
Source dataset
uspto-grants-2013_07
Patent number
US08481524B2

Reaction notes

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