HCID 67355236, compound → HCID 67354241, compound

HRID 2272287Notes

Reaction equation

HRID 2272287 reaction equation
[CH:1]1([C:4]2[C:5]([N+:24]([O-])=O)=[CH:6][C:7]3[O:11][C:10]([C:12]4[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=4)=[C:9]([C:19]([O:21][CH3:22])=[O:20])[C:8]=3[CH:23]=2)[CH2:3][CH2:2]1>C(OCC)(=O)C.Cl.[Pd].ClCCl>[NH2:24][C:5]1[C:4]([CH:1]2[CH2:3][CH2:2]2)=[CH:23][C:8]2[C:9]([C:19]([O:21][CH3:22])=[O:20])=[C:10]([C:12]3[CH:17]=[CH:16][C:15]([F:18])=[CH:14][CH:13]=3)[O:11][C:7]=2[CH:6]=1

Participants

6

Reactant 1

HCID 67355236HCID 67355236, compound

Product 1

HCID 67354241HCID 67354241, compound

Reagents, catalysts & solvents 4

HCID 313Hydrochloric AcidCatalystHCID 23938PalladiumCatalystHCID 6344DichloromethaneSolventHCID 8857Ethyl AcetateSolvent

Procedure

A solution of methyl 5-cyclopropyl-2-(4-fluorophenyl)-6-nitro-1-benzofuran-3-carboxylate (3.175 g, 8.94 mmol) in ethyl acetate (250 mL) containing 2M HCl (17 drops) was stirred with 10% palladium on carbon (0.951 g, 0.894 mmol) under an atmosphere of hydrogen at 21° C. for 16 hours. The reaction mixture was filtered through celite and the filtrate was evaporated under vacuum to give a dark green solid. This was dissolved in dichloromethane, washed with sodium bicarbonate solution, separated by hydrophobic frit, then evaporated to dryness and purified by flash chromatography, eluting over silica gel with a gradient of 0-30% ethyl acetate in cyclohexane. Appropriate fractions were combined and evaporated under vacuum to give the methyl 6-amino-5-cyclopropyl-2-(4-fluorophenyl)-1-benzofuran-3-carboxylate. LCMS (m/z, ES+)=326 (M+H+).

Workup

  1. filtrationThe reaction mixture was filtered through celite
  2. customthe filtrate was evaporated under vacuum
  3. customto give a dark green solid
  4. washwashed with sodium bicarbonate solution
  5. customseparated by hydrophobic frit
  6. customevaporated to dryness
  7. custompurified by flash chromatography
  8. washeluting over silica gel with a gradient of 0-30% ethyl acetate in cyclohexane
  9. customevaporated under vacuum

Sources & evidence

ORD record
ord-4d41b89c1c0d402bbb04e7f217a2a181
Source dataset
uspto-grants-2015_09
Patent number
US09119868B2

Reaction notes

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