Acetic Acid → HCID 42630563, compound

HRID 1399484Notes

Reaction equation

HRID 1399484 reaction equation
[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH:10]=O)=[CH:9][C:4]=2[CH:3]=[CH:2]1.[NH2:12][C:13]1[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=1.C(O)(=O)C.C(O[BH-](OC(=O)C)OC(=O)C)(=O)C.[Na+]>ClCCCl>[O:1]1[C:5]2[CH:6]=[CH:7][C:8]([CH2:10][NH:12][C:13]3[CH:18]=[CH:17][N:16]=[CH:15][CH:14]=3)=[CH:9][C:4]=2[CH:3]=[CH:2]1

Participants

6

Reactant 4

HCID 176Acetic AcidHCID 17274-AminopyridineHCID 27738751-Benzofuran-5-carbaldehydeHCID 5049666Sodium triacetoxyborohydride

Product 1

HCID 42630563HCID 42630563, compoundYield 13%

Reagents, catalysts & solvents 1

HCID 111,2-DichloroethaneSolvent

Conditions

Temperature
60 °C

Procedure

Benzofuran-5-carbaldehyde (330 mg, 2.19 mmol, 1.0 equiv.) and 4-aminopyridine (227 mg, 2.41 mmol, 1.1 equiv.) were combined in 1,2-dichloroethane (22 mL) and treated with acetic acid (138 μL, 2.41 mmol, 1.1 equiv.) and sodium triacetoxyborohydride (969 mg, 4.34 mmol, 1.98 equiv.). The mixture was stirred at 60° C. overnight, and then quenched by addition of saturated NaHCO3 solution. The two phases were separated and the water layer was extracted twice with ethyl acetate. The combined organic extract was dried over Na2SO4, filtered and concentrated in vacuo. The residue was purified with flash column chromatography on silica gel, eluting with ethyl acetate/dichloromethane/methanol to afford N-(benzofuran-5-ylmethyl)pyridin-4-amine as a white solid (62 mg, 13% yield). Mass: 225 (MH)+. Purity >99% (HPLC).

Workup

  1. customquenched by addition of saturated NaHCO3 solution
  2. customThe two phases were separated
  3. extractionthe water layer was extracted twice with ethyl acetate
  4. extractionThe combined organic extract
  5. dry with materialwas dried over Na2SO4
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo
  8. customThe residue was purified with flash column chromatography on silica gel
  9. washeluting with ethyl acetate/dichloromethane/methanol

Sources & evidence

ORD record
ord-307c93d5ae3c44c1b2864f1d538068ce
Source dataset
uspto-grants-2014_12
Patent number
US08906647B2

Reaction notes

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