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Tris(furan-2-yl)phosphane → HCID 178432469, compound

HRID 2363704
Notes
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Reaction equation

HRID 2363704 reaction equation
C[Sn](C)(C)[C:3]1[CH:4]=[CH:5][C:6]2[N:7]([CH:9]=[C:10]([C:12]([NH:14][C:15]3[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=3)=[O:13])[N:11]=2)[CH:8]=1.[CH3:23][C:24]1[NH:25][CH:26]=[C:27](I)[N:28]=1.O1C=CC=C1P(C1OC=CC=1)C1OC=CC=1>C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.C1C=CC(/C=C/C(/C=C/C2C=CC=CC=2)=O)=CC=1.[Pd].O1CCCC1>[CH3:23][C:24]1[NH:25][CH:26]=[C:27]([C:3]2[CH:4]=[CH:5][C:6]3[N:7]([CH:9]=[C:10]([C:12]([NH:14][C:15]4[CH:20]=[CH:19][CH:18]=[CH:17][CH:16]=4)=[O:13])[N:11]=3)[CH:8]=2)[N:28]=1
ParticipantsProcedureWorkupSources & evidenceReaction notes

Participants

6

Reactant 3

HCID 521585Tris(furan-2-yl)phosphaneHCID 441359416-trimethylstannyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamide2×HCID 178433060HCID 178433060, compound

Product 1

HCID 178432469HCID 178432469, compoundYield 8.8%

Reagents, catalysts & solvents 2

HCID 6505921
(1E,4E)-1,5-diphenylpenta-1,4-dien-3-one; palladium
Catalyst
HCID 8028TetrahydrofuranSolvent

Procedure

400 mg of 6-trimethylstannyl-N-phenylimidazo[1,2-a]pyridine-2-carboxamide (Intermediate 4), 229 mg of 2-methyl-4-iodo-1H-imidazole, 8 mL of tetrahydrofuran, 9.1 mg of bis(dibenzylideneacetone)palladium and 4.6 mg of tris(2-furyl)phosphine are placed in a microwave tube. The reaction mixture is heated for 50 minutes in a microwave machine set at 130° C. and then concentrated to dryness. The residue is taken up in 3.5 mL of N,N-dimethylformamide and a further 150 mg of 2-methyl-4-iodo-1H-imidazole, 10 mg of bis(dibenzylideneacetone)palladium and 5 mg of tris(2-furyl)phosphine are added, followed by heating again for 40 minutes in a microwave machine set at 120° C. The reaction mixture is filtered, the insoluble matter is rinsed with methanol and dichloromethane and the combined filtrates are concentrated under reduced pressure. The residue is chromatographed on a silica cartridge, eluting with dichloromethane and then with a 90/10 mixture of dichloromethane and methanol. The fractions containing the pure expected product are combined and evaporated to dryness under reduced pressure to give 28 mg of 6-(2-methyl-1H-imidazol-4-yl)-N-phenylimidazo[1,2-a]pyridine-2-carboxamide in the form of a beige-coloured solid.

Workup

  1. temperatureThe reaction mixture is heated for 50 minutes in a microwave machine
  2. customset at 130° C.
  3. concentrationconcentrated to dryness
  4. additiona further 150 mg of 2-methyl-4-iodo-1H-imidazole, 10 mg of bis(dibenzylideneacetone)palladium and 5 mg of tris(2-furyl)phosphine are added
  5. temperatureby heating again for 40 minutes in a microwave machine
  6. customset at 120° C
  7. filtrationThe reaction mixture is filtered
  8. washthe insoluble matter is rinsed with methanol and dichloromethane
  9. concentrationthe combined filtrates are concentrated under reduced pressure
  10. customThe residue is chromatographed on a silica cartridge
  11. washeluting with dichloromethane
  12. additionwith a 90/10 mixture of dichloromethane and methanol
  13. additionThe fractions containing the pure expected product
  14. customevaporated to dryness under reduced pressure

Sources & evidence

ORD record
ord-785f6c94508a472390759f6e289f3b23
Source dataset
uspto-grants-2014_04
DOI
10.6084/m9.figshare.5104873.v1
Patent number
US08691990B2

Reaction notes

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