Sodium hydride → HCID 18704224, compound

HRID 2288296Notes

Reaction equation

HRID 2288296 reaction equation
[H-].[Na+].[O:3]=[C:4]1[N:8]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([C:17]([F:20])([F:19])[F:18])[CH:10]=2)[C:7](=[O:21])[C:6]2([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[NH:5]1.[H][H].C[Si](C)(C)[O:31][CH2:32][CH2:33][CH2:34][CH2:35]I>CN(C)C=O>[O:3]=[C:4]1[N:8]([C:9]2[CH:16]=[CH:15][C:12]([C:13]#[N:14])=[C:11]([C:17]([F:20])([F:18])[F:19])[CH:10]=2)[C:7](=[O:21])[C:6]2([CH2:26][CH2:25][CH2:24][CH2:23][CH2:22]2)[N:5]1[CH2:35][CH2:34][CH2:33][CH2:32][OH:31]

Participants

6

Reactant 4

HCID 24758Sodium hydrideHCID 10978586Silane, (4-iodobutoxy)trimethyl-HCID 18704219HCID 18704219, compoundHCID 178418361HCID 178418361, compound

Product 1

HCID 18704224HCID 18704224, compoundYield 76.6%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

28 mg of 50% sodium hydride and 3 ml of dimethylformamide are introduced, agitation is carried out at ambient temperature for 5 minutes, 170 mg of the product obtained in Stage 3 above is added and the whole is left under agitation for 20 minutes until the release of hydrogen has stopped. 202 mg of O-trimethylsilyl-4-iodo-n-butanol is then added and the reaction medium is left under agitation for 2 hours. After hydrolysis using saturated ammonium chloride, extraction is carried out with ethyl acetate. The organic phases are combined, washed with water, dried, filtered and concentrated. The residue is solubilized in 10 ml of methanol and 0.5 ml of 2N hydrochloric acid is added. After agitation for 5 minutes, the solution is neutralized by the addition of saturated sodium hydrogen carbonate and extraction is carried out with ethyl acetate. The organic phases are combined, dried, filtered and concentrated. After chromatography on silica eluting with methylene chloride-acetone: 9-1, 158 mg of expected product (white solid) is obtained. M.p.=145° C.

Workup

  1. waitthe reaction medium is left under agitation for 2 hours
  2. customAfter hydrolysis
  3. extractionammonium chloride, extraction
  4. washwashed with water
  5. customdried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. addition0.5 ml of 2N hydrochloric acid is added
  9. waitAfter agitation for 5 minutes
  10. additionthe solution is neutralized by the addition of saturated sodium hydrogen carbonate and extraction
  11. customdried
  12. filtrationfiltered
  13. concentrationconcentrated

Sources & evidence

ORD record
ord-6118d6b7654447e183a59545e74e62c1
Source dataset
uspto-grants-2000_07
Patent number
US06087509

Reaction notes

Loading…