Tributylphenyltin → HCID 18404034, compound

HRID 1017633Notes

Reaction equation

HRID 1017633 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[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=1)CCC>CN(C=O)C.O.[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>[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[CH:36]=[CH:35][CH:34]=[CH:33][CH:32]=3)[CH:16]=[C:11]2[N:10]=[N:9]1

Participants

6

Reactant 2

HCID 607632TributylphenyltinHCID 18404041HCID 18404041, compound

Product 1

HCID 18404034HCID 18404034, compoundYield 52%

Reagents, catalysts & solvents 3

HCID 11979704Tetrakis(triphenylphosphine)palladiumCatalystHCID 962WaterSolventHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A solution of 3-(2-fluorophenyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-6-bromo-1,2,3-triazolo[4,5-b]pyridine (0.15 g, 0.37 mmol), tributylphenyltin (0.14 ml, 0.44 mmol) and tetrakis(triphenylphosphine)-palladium(0) (0.02 g, 5 mol %) in dry DMF (2 ml) was purged with nitrogen and heated in a sealed tube at 100° C. for 24 h. The mixture was cooled, diluted with water (50 ml) and extracted with 10% methanol-dichloromethane (2×25 ml). The extracts were washed with brine (20 ml), dried (Na2SO4), filtered and concentrated. Flash column chromatography on silica gel, eluting with 2% methanol-dichloromethane, gave a yellow oil that solidified on trituration and washing with diethyl ether (2 ml). The material was recrystallised from ethyl acetate-hexane to give 3-(2-fluorophenyl)-5-(2-methyl-2H-1,2,4-triazol-3-ylmethoxy)-6-phenyl-1,2,3-triazolo[4,5-b]pyridine (0.077 g, 52%) as a cream-coloured solid, m.p. 144-146° C. (EtOAc-hexane). Found: C, 62.00; H, 4.00; N, 24.01. C21H16N7OF.0.33(H2O) requires C, 61.91; H, 4.12; N, 24.07%. δH (360 MHz; CDCl3) 3.64 (3H, s), 5.56 (2H, s), 7.38-7.47 (5H, m), 7.53 (2H, dd, J=8 and 1), 7.56-7.62 (1H, m), 7.71 (1H, dd, J=8 and 8), 7.82 (1H, s) and 8.32 (1H, s); m/z (ES+) 402 (M+H+).

Workup

  1. temperatureThe mixture was cooled
  2. extractionextracted with 10% methanol-dichloromethane (2×25 ml)
  3. washThe extracts were washed with brine (20 ml)
  4. dry with materialdried (Na2SO4)
  5. filtrationfiltered
  6. concentrationconcentrated
  7. washFlash column chromatography on silica gel, eluting with 2% methanol-dichloromethane
  8. customgave a yellow oil that
  9. washwashing with diethyl ether (2 ml)
  10. customThe material was recrystallised from ethyl acetate-hexane

Sources & evidence

ORD record
ord-784aa158411342e3b6a8fc51ef899c88
Source dataset
uspto-grants-2002_11
Patent number
US06479506B1

Reaction notes

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