Sodium hydride → HCID 86641878, compound

HRID 1640918Notes

Reaction equation

HRID 1640918 reaction equation
[H-].[Na+].[C:3]([O:7][C:8](=[O:20])[NH:9][CH:10]([C:12]1[CH:13]=[N:14][C:15]([F:19])=[CH:16][C:17]=1[I:18])[CH3:11])([CH3:6])([CH3:5])[CH3:4].[F:21][CH2:22][CH2:23]I>C(Cl)(Cl)Cl.C(O)(C)C>[F:19][C:15]1[N:14]=[CH:13][C:12]([CH:10]([N:9]([CH2:23][CH2:22][F:21])[C:8](=[O:20])[O:7][C:3]([CH3:4])([CH3:5])[CH3:6])[CH3:11])=[C:17]([I:18])[CH:16]=1

Participants

5

Reactant 3

HCID 24758Sodium hydrideHCID 69804Ethane, 1-fluoro-2-iodo-HCID 66738218HCID 66738218, compound

Product 1

HCID 86641878HCID 86641878, compoundYield 41.5%

Reagents, catalysts & solvents 1

HCID 21906603Chloroform isopropyl alcoholSolvent

Procedure

Add sodium hydride (58.9 mg, 2.46 mmol) to a solution of [1-(6-fluoro-4-iodo-pyridin-3-yl)-ethyl]-carbamic acid tert-butyl ester (300 mg, 819 μmol) at 0° C. Stir the mixture at 0° C. to RT for 1 h. Add 1-fluoro-2-iodo-ethane (570 mg, 3.28 mmol). Stir the mixture at RT for 4 h and then at 50° C. overnight. Dilute the mixture with chloroform/IPA (3/1, 100 mL) and wash with water/aqueous saturated sodium chloride. Dry the organic phase over sodium sulfate and concentrate in vacuo to give the crude product. Purify the crude product by FCC (20% ethyl acetate in hexane) to give 140 mg of the title compound (41%). MS (ES) m/z 413 [M+1]+.

Workup

  1. stirringStir the mixture at RT for 4 h
  2. customat 50° C.
  3. customovernight
  4. washwash with water/aqueous saturated sodium chloride
  5. dry with materialDry the organic phase over sodium sulfate
  6. concentrationconcentrate in vacuo
  7. customto give the crude product
  8. customPurify the crude product by FCC (20% ethyl acetate in hexane)

Sources & evidence

ORD record
ord-2d853eef79084126a49cea858949e589
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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