Tetrahydrofuran → HCID 21285522, compound

HRID 2231661Notes

Reaction equation

HRID 2231661 reaction equation
[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N:9]2[CH:13]=[N:12][N:11]=[CH:10]2)=[CH:4][C:3]=1I.C1C[O:18][CH2:17]C1>[Pd].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[NH2:1][C:2]1[C:7]([CH3:8])=[CH:6][C:5]([N:9]2[CH:13]=[N:12][N:11]=[CH:10]2)=[CH:4][C:3]=1[CH:17]=[O:18]

Participants

4

Reactant 2

HCID 8028TetrahydrofuranHCID 21285538HCID 21285538, compound

Product 1

HCID 21285522HCID 21285522, compound

Reagents, catalysts & solvents 1

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalyst

Procedure

A stirred mixture of 4-(4-amino-3-iodo-5-methylphenyl)-1,2,4-triazole (3.0 g) and tetrakis (triphenylphosphine) palladium (0) (1.0 g) in THF (300 cm3) was deoxygenated with a stream of nitrogen for 0.5 hours. The mixture was then placed under carbon monoxide (ca 2 atmospheres pressure), warmed to 50°, and a solution of tri-n-butyltin hydride (3.2 g) in THF (200 cm3) was added dropwise over 4 hours. After a further 0.5 hours, the mixture was poured onto an aqueous solution of potassium fluoride (10 g) in water (200 cm3) and the mixture was extracted with dichloromethane (5×200 cm3). The combined and dried (MgSO4) extracts were evaporated in vacuo and the residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark]), eluting with dichloromethane:methanol, 9:1. Combination and evaporation of the appropriate fractions gave a solid which was recrystallised from ethyl acetate-methanol to afford the title compound, m.p. 250°-252° (1.87 g), characterised spectroscopically to be identical to the product of Preparation 30.

Workup

  1. customwas deoxygenated with a stream of nitrogen for 0.5 hours
  2. temperaturewarmed to 50°
  3. additiona solution of tri-n-butyltin hydride (3.2 g) in THF (200 cm3) was added dropwise over 4 hours
  4. additionthe mixture was poured onto an aqueous solution of potassium fluoride (10 g) in water (200 cm3)
  5. extractionthe mixture was extracted with dichloromethane (5×200 cm3)
  6. dry with materialdried (MgSO4) extracts
  7. customwere evaporated in vacuo
  8. customthe residue was chromatographed on silica (Merck "MK 60.9385" [Trade Mark])
  9. washeluting with dichloromethane
  10. customCombination and evaporation of the appropriate fractions
  11. customgave a solid which
  12. customwas recrystallised from ethyl acetate-methanol

Sources & evidence

ORD record
ord-394cb3f3ffd14429acfe89545f912df5
Source dataset
uspto-grants-1988_11
Patent number
US04783467

Reaction notes

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