Sodium Carbonate → HCID 19921681, compound

HRID 1463340Notes

Reaction equation

HRID 1463340 reaction equation
[NH2:1][C:2]1[CH:12]=[CH:11][C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])=[CH:4][C:3]=1I.[CH3:14][C:15]([Si:18]([CH3:30])([CH3:29])[O:19][CH2:20][CH2:21][CH2:22][C:23]#[C:24][Si:25]([CH3:28])([CH3:27])[CH3:26])([CH3:17])[CH3:16].C(=O)([O-])[O-].[Na+].[Na+]>[Cl-].C([N+](CCCC)(CCCC)CCCC)CCC.CN(C=O)C.C([O-])(=O)C.[Pd+2].C([O-])(=O)C.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>[CH3:17][C:15]([Si:18]([CH3:29])([CH3:30])[O:19][CH2:20][CH2:21][CH2:22][C:23]1[C:3]2[C:2](=[CH:12][CH:11]=[C:5]([C:6]([O:8][CH2:9][CH3:10])=[O:7])[CH:4]=2)[NH:1][C:24]=1[Si:25]([CH3:26])([CH3:27])[CH3:28])([CH3:14])[CH3:16]

Participants

8

Reactant 3

HCID 10340Sodium CarbonateHCID 459320Ethyl 4-amino-3-iodobenzoateHCID 10923628HCID 10923628, compound

Product 1

HCID 19921681HCID 19921681, compoundYield 65%

Reagents, catalysts & solvents 4

HCID 11776TriphenylphosphineCatalystHCID 70681Tetrabutylammonium ChlorideCatalystHCID 167845palladium(II) acetateCatalystHCID 6228DimethylformamideSolvent

Procedure

A mixture of ethyl 4-amino-3-iodobenzoate {Hirschfeld et al. J. Med Chem. 1992, 35, 2231-2238.} (7.80 g, 26.8 mmol), [5-[[(1,1-dimethylethyl)dimethylsilyl]oxy]-1-pentynyl]tri methylsilane (9.41 g, 34.8 mmol), tetra-n-butylammonium chloride (7.44 g, 26.8 mmol), sodium carbonate (14.20 g, .134 mol), triphenylphosphine (0.35 g, 1.3 mmol), and palladium (II) acetate (0.30 g, 1.3 mmol) in 200 mL of DMF, was heated at 98° C. under N2 for 2 h. The solution was cooled, and the bulk of the DMF was removed in vacuo. The mixture was diluted with ethyl acetate, and the organic solution was washed with aqueous NaHCO3, dried (brine, MgSO4), filtered, and concentrated in vacuo. Silica gel chromatography (10:1 hexanes-EtOAc) of the concentrate yielded the title compound (7.49 g, 65%) as a crystalline solid. Recrystallization from hexanes provided an analytical sample as a white crystalline solid: mp 115°-116° C. Anal. Calcd for C23H39N1O3Si2 : C 63.69; H, 9.06; N, 3.23. Found: C, 63.54; H, 9.11; N, 3.17.

Workup

  1. temperatureThe solution was cooled
  2. customthe bulk of the DMF was removed in vacuo
  3. additionThe mixture was diluted with ethyl acetate
  4. washthe organic solution was washed with aqueous NaHCO3
  5. dry with materialdried (brine, MgSO4)
  6. filtrationfiltered
  7. concentrationconcentrated in vacuo

Sources & evidence

ORD record
ord-9751c2fb32444fedb2c1fd347956805d
Source dataset
uspto-grants-1994_04
Patent number
US05300506

Reaction notes

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