Sodium Carbonate → HCID 10729768, compound

HRID 1459718Notes

Reaction equation

HRID 1459718 reaction equation
[Cl-].[Li+].C(=O)([O-])[O-].[Na+].[Na+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.C([Si]([O:35][CH2:36][CH2:37][CH2:38][C:39]#[C:40][Si](CC)(CC)CC)(CC)CC)C.I[C:49]1[CH:55]=[C:54]([CH2:56][N:57]2[CH:61]=[N:60][CH:59]=[N:58]2)[CH:53]=[CH:52][C:50]=1[NH2:51]>CN(C)C=O.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[N:57]1([CH2:56][C:54]2[CH:53]=[C:52]3[C:50](=[CH:49][CH:55]=2)[NH:51][CH:40]=[C:39]3[CH2:38][CH2:37][CH2:36][OH:35])[CH:61]=[N:60][CH:59]=[N:58]1

Participants

8

Reactant 5

HCID 10340Sodium CarbonateHCID 11776TriphenylphosphineHCID 433294Lithium ChlorideHCID 111201102-Iodo-4-[(1H-1,2,4-triazol-1-yl)methyl]anilineHCID 53696250Triethyl{5-[(triethylsilyl)oxy]pent-1-yn-1-yl}silane

Product 1

HCID 10729768HCID 10729768, compoundYield 56%

Reagents, catalysts & solvents 2

HCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Conditions

Temperature
100 °C

Procedure

A mixture of palladium acetate (0.78 g), lithium chloride (1.47 g), sodium carbonate (18.49 g), triphenylphosphine (1.8 g), 5-triethylsilyl-4-pentyn-1-ol triethylsilyl ether (16.3 g) and 2-iodo-4-[(1,2,4-triazol-1-yl)methyl]aniline (10.0 g) in degassed anhydrous dimethylformamide (400 ml) was heated at 100° C. for 10 h, under nitrogen. After cooling, the reaction was filtered, concentrated, and the residue was partitioned between water and ethyl acetate. The organic phase was dried (MgSO4), concentrated and the residue was treated with 5N hydrochloric acid/methanol (1:3; 400 ml) for 3 h at room temperature. The methanol was removed under vacuum, the aqueous residue was basified with sodium carbonate solution and it was extracted with ethyl acetate. The combined organic extracts were dried (MgSO4) and concentrated. Flash chromatography of the residue (silica gel, dichloromethane/methanol, 95:5) followed by trituration with petroleum ether, gave the title compound (56%) as a beige solid. δH (360 MHz, DMSO-d6) 1.74-1.82 (2H, m), 2.66-2.70 (2H, m), 3.43-3.49 (2H, m), 4.41-4.44 (1H, m), 5.42 (2H, s), 7.01-7.04 (1H, m), 7.11-7.12 (1H, m), 7.28-7.30 (1H, m), 7.51 (1H, s), 7.93 (1H, s), 8.60 (1H, s), 10.79 (1H, s).

Workup

  1. temperatureAfter cooling
  2. filtrationthe reaction was filtered
  3. concentrationconcentrated
  4. customthe residue was partitioned between water and ethyl acetate
  5. dry with materialThe organic phase was dried (MgSO4)
  6. concentrationconcentrated
  7. additionthe residue was treated with 5N hydrochloric acid/methanol (1:3; 400 ml) for 3 h at room temperature
  8. customThe methanol was removed under vacuum
  9. extractionwas extracted with ethyl acetate
  10. dry with materialThe combined organic extracts were dried (MgSO4)
  11. concentrationconcentrated

Sources & evidence

ORD record
ord-656a85254ac840a0986b5d14e5f3b9a4
Source dataset
uspto-grants-1998_12
Patent number
US05854268

Reaction notes

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