2-(Tributylstannyl)furan → HCID 9886734, compound

HRID 1017636Notes

Reaction equation

HRID 1017636 reaction equation
[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2=[N:13][C:14]([O:18][CH2:19][C:20]3[N:21]([CH3:25])[N:22]=[CH:23][N:24]=3)=[C:15](Br)[CH:16]=[C:11]2[N:10]=[N:9]1.C([Sn](CCCC)(CCCC)[C:31]1[O:32][CH:33]=[CH:34][CH:35]=1)CCC>CN(C=O)C.O.C1C=CC([P]([Pd]([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)([P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)[P](C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)(C2C=CC=CC=2)C2C=CC=CC=2)=CC=1>[F:1][C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][C:3]=1[N:8]1[C:12]2=[N:13][C:14]([O:18][CH2:19][C:20]3[N:21]([CH3:25])[N:22]=[CH:23][N:24]=3)=[C:15]([C:31]3[O:32][CH:33]=[CH:34][CH:35]=3)[CH:16]=[C:11]2[N:10]=[N:9]1

Participants

6

Reactant 2

HCID 43936882-(Tributylstannyl)furanHCID 18404041HCID 18404041, compound

Product 1

HCID 9886734HCID 9886734, compoundYield 74%

Reagents, catalysts & solvents 3

HCID 178418397HCID 178418397, compoundCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of 3-(2-fluorophenyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-6-bromo-1,2,3-triazolo[4,5-b]pyridine (0.12 g, 0.29 7 mmol) (Example 3, step c), 2-tributylstannylfuran (0.19 ml, 0.60 mmol) and tetrakis(triphenylphosphine)palladium(0) (0.02 g, 5 mol %) in DMF (3 ml) was heated in a sealed tube at 100° C. for 7 h. The solution was cooled, diluted with water (40 ml) and extracted with 10% methanol-dichloromethane (2×20 ml). The extracts were dried (Na2SO4), filtered and concentrated. The residue was dissolved in ethyl acetate-dichloromethane and decolourised with charcoal (50 mg). The filtrate was concentrated to give 3-(2-fluorophenyl)-6-(2-furyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-1,2,3-triazolo[4,5-b]pyridine (0.086 g, 74%) as an off-white solid, m.p. 170-173° C. Found: C, 57.28; H, 3.67. C19H14FN7O2.0.5(H2O) requires C, 57.00; H, 3.78. δH (400 MHz; CDCl3) 3.84 (3H, s), 5.66 (2H, s), 6.51 (1H, dd, J=3 and 2), 6.93 (1H, d, J=3), 7.37-7.43 (2H, m), 7.56-7.60 (2H, m), 7.71 (1H, dd, J=8 and 8), 7.90 (1H, s) and 8.80 (1H, s); m/z (ES+) 392 (M+H+).

Workup

  1. temperatureThe solution was cooled
  2. extractionextracted with 10% methanol-dichloromethane (2×20 ml)
  3. dry with materialThe extracts were dried (Na2SO4)
  4. filtrationfiltered
  5. concentrationconcentrated
  6. dissolutionThe residue was dissolved in ethyl acetate-dichloromethane
  7. concentrationThe filtrate was concentrated

Sources & evidence

ORD record
ord-17cca7880ebe47bd943e46e8d7593c38
Source dataset
uspto-grants-2002_11
Patent number
US06479506B1

Reaction notes

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