Iodine → HCID 91377919, compound

HRID 1640886Notes

Reaction equation

HRID 1640886 reaction equation
[CH3:1][C:2]1[N:7]=[CH:6][C:5]([CH:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9])=[CH:4][CH:3]=1.C([Li])(C)(C)C.[I:23]I>C1COCC1>[I:23][C:4]1[CH:3]=[C:2]([CH3:1])[N:7]=[CH:6][C:5]=1[CH:8]([NH:10][C:11](=[O:17])[O:12][C:13]([CH3:16])([CH3:15])[CH3:14])[CH3:9]

Participants

5

Reactant 3

HCID 807IodineHCID 66738394HCID 66738394, compoundHCID 178418306HCID 178418306, compound

Product 1

HCID 91377919HCID 91377919, compoundYield 5.9%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

Add a solution of tert-butyl 1-(6-methylpyridin-3-yl)ethylcarbamate (6.85 g, 29 mmol) to a solution of tert-butyllithium (51.1 mL, 87 mmol) in THF (70 mL) at −78° C. in THF (20 mL) under N2 using a double-tipped needle. After 30 min, add iodine (11.0 g, 43.5 mmol) in THF (25 mL) over 30 min at −78° C. Stir for 1 h and then warm up to RT. Quench with water, extract in ethyl acetate, wash with saturated aqueous sodium chloride, and dry over Na2SO4. Purify on column chromatography 5% to 50% ethyl acetate in hexanes to obtain the title compound (620 mg). MS (ES) m/z 363 [M+1]+.

Workup

  1. customQuench with water
  2. extractionextract in ethyl acetate
  3. washwash with saturated aqueous sodium chloride
  4. dry with materialdry over Na2SO4
  5. customPurify on column chromatography 5% to 50% ethyl acetate in hexanes

Sources & evidence

ORD record
ord-6f45df87d6704e6da6860a8f04cdb863
Source dataset
uspto-grants-2012_02
Patent number
US08114872B2

Reaction notes

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