Trimethylsilyl iodide → HCID 135848038, compound

HRID 497707Notes

Reaction equation

HRID 497707 reaction equation
C[Si](I)(C)C.[O:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][C:19]=1[C:20]1[CH:25]=[CH:24][C:23]([O:26]CC3C=CC=CC=3)=[CH:22][CH:21]=1)[NH:16][N:15]=[C:14]2[NH:34][C:35](=[O:39])[CH2:36][CH2:37][CH3:38]>CO>[O:6]1[CH:10]=[CH:9][CH:8]=[C:7]1[C:11]1[CH:12]=[C:13]2[C:17](=[CH:18][C:19]=1[C:20]1[CH:21]=[CH:22][C:23]([OH:26])=[CH:24][CH:25]=1)[NH:16][N:15]=[C:14]2[NH:34][C:35](=[O:39])[CH2:36][CH2:37][CH3:38]

Participants

4

Reactant 2

HCID 85247Trimethylsilyl iodideHCID 22319507HCID 22319507, compound

Product 1

HCID 135848038HCID 135848038, compoundYield 1.7%

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Procedure

10 cm3 of trimethylsilyl iodide are added to 750 mg of N-[(5-(2-furyl)-6-[4-(phenylmethoxy)phenyl]-1H-indazol-3-yl)]butanamide, described previously, and the mixture is refluxed for 18 hours. 40 cm3 of methanol are added and the reaction medium and the mixture is refluxed for 10 minutes and then concentrated to dryness under reduced pressure (2 kPa; 50° C.). The residue is taken up in 75 cm3 of ethyl acetate and 50 cm3 of tetrahydrofuran and the organic phase is washed with 2×75 cm3 of 10% sodium thiosulphate solution and then with 75 cm3 of saturated sodium chloride solution. The organic phase is separated out after settling of the phases has taken place, dried over magnesium sulphate, filtered and then concentrated to dryness under reduced pressure to give 700 mg of crude product, which is purified by chromatography under an argon pressure of 50 kPa, on a column of silica gel (particle size 40-60 μm; diameter 2.5 cm), eluting with a cyclohexane/ethyl acetate mixture (50/50 by volume). The fractions containing the expected product are combined and evaporated under reduced pressure (2 kPa; 50° C.); the residue is taken up in 3 cm3 of ethyl acetate, filtered off, washed with 2 cm3 of ethyl acetate, then with 15 cm3 of diisopropyl ether and dried (90 Pa; 45° C.) to give 10 mg of N-[5-(2-furyl)-6-(4-hydroxyphenyl)-1H-indazol-3-yl]butanamide in the form of white crystals melting at 190° C.

Workup

  1. temperaturethe mixture is refluxed for 18 hours
  2. temperaturethe reaction medium and the mixture is refluxed for 10 minutes
  3. concentrationconcentrated to dryness under reduced pressure (2 kPa; 50° C.)
  4. wash50 cm3 of tetrahydrofuran and the organic phase is washed with 2×75 cm3 of 10% sodium thiosulphate solution
  5. customThe organic phase is separated out
  6. dry with materialdried over magnesium sulphate
  7. filtrationfiltered
  8. concentrationconcentrated to dryness under reduced pressure
  9. customto give 700 mg of crude product, which
  10. customis purified by chromatography under an argon pressure of 50 kPa
  11. washon a column of silica gel (particle size 40-60 μm; diameter 2.5 cm), eluting with a cyclohexane/ethyl acetate mixture (50/50 by volume)
  12. additionThe fractions containing the expected product
  13. customevaporated under reduced pressure (2 kPa; 50° C.)
  14. filtrationfiltered off
  15. washwashed with 2 cm3 of ethyl acetate
  16. dry with materialwith 15 cm3 of diisopropyl ether and dried (90 Pa; 45° C.)

Sources & evidence

ORD record
ord-1e3dbdb5d5c6465f94160e6937f47aba
Source dataset
uspto-grants-2005_09
Patent number
US06949579B2

Reaction notes

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