Methyl iodide → HCID 11447978, compound

HRID 1913368Notes

Reaction equation

HRID 1913368 reaction equation
[H-].[Na+].[N:3]1[CH:8]=[CH:7][CH:6]=[C:5]([C:9]#[C:10][CH2:11][NH:12][C:13](=[O:19])[O:14][C:15]([CH3:18])([CH3:17])[CH3:16])[CH:4]=1.I[CH3:21]>C1COCC1>[CH3:21][N:12]([CH2:11][C:10]#[C:9][C:5]1[CH:4]=[N:3][CH:8]=[CH:7][CH:6]=1)[C:13](=[O:19])[O:14][C:15]([CH3:16])([CH3:18])[CH3:17]

Participants

5

Reactant 3

HCID 6328Methyl iodideHCID 24758Sodium hydrideHCID 70832777tert-Butyl [3-(pyridin-3-yl)prop-2-yn-1-yl]carbamate

Product 1

HCID 11447978HCID 11447978, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 8028TetrahydrofuranSolvent3×

Procedure

To a solution of sodium hydride (60% dispersion in mineral oil, 30 mg, 0.95 mmol) in anhydrous THF (3 mL) at 0° C. was added a solution of 47 (109 mg, 0.47 mmol) in anhydrous THF (2 mL) dropwise over 15 min. To the resultant solution was added a solution of iodomethane (150 μL, 2.42 mmol) in THF (5 mL) over 10 min, the ice bath was removed and the solution was stirred at ambient temperature for 16 h. The reaction was stopped by the addition of water (5 mL) and the aqueous fraction was extracted with EtOAc (3×20 mL), washed with water, dried (Na2SO4), filtered and the solvent was removed in vacuo. The crude material was chromatographed on silica gel (EtOAc/Hex, 25/75, Rf=0.18) to afford the title compound 49 (69 mg, 60% yield) as a yellow oil: 1H NMR (CDCl3) δ 8.65 (s, 1H), 8.52 (m, 1H), 7.69 (m, 1H), 7.24 (m, 1H), 4.29 (s, 2H), 2.97 (s, 3H), 2.97 (s, 9H); LRMS (ESI) m/z calcd for C14H19N2O2 [M H]+ 247. found 247.

Workup

  1. customthe ice bath was removed
  2. additionThe reaction was stopped by the addition of water (5 mL)
  3. extractionthe aqueous fraction was extracted with EtOAc (3×20 mL)
  4. washwashed with water
  5. dry with materialdried (Na2SO4)
  6. filtrationfiltered
  7. customthe solvent was removed in vacuo
  8. customThe crude material was chromatographed on silica gel (EtOAc/Hex, 25/75, Rf=0.18)

Sources & evidence

ORD record
ord-7c66ec7664fc45c2b2e23ff3918182ca
Source dataset
uspto-grants-2013_12
Patent number
US08609708B2

Reaction notes

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