Imidazole → HCID 58573628, compound

HRID 1048597Notes

Reaction equation

HRID 1048597 reaction equation
[I:1]I.N1C=CN=C1.C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1.[CH3:27][O:28][C:29]1[N:34]=[C:33]([CH2:35]O)[CH:32]=[CH:31][CH:30]=1>ClCCl>[I:1][CH2:35][C:33]1[CH:32]=[CH:31][CH:30]=[C:29]([O:28][CH3:27])[N:34]=1

Participants

6

Reactant 4

HCID 795ImidazoleHCID 807IodineHCID 11776TriphenylphosphineHCID 12325389(6-Methoxypyridin-2-yl)methanol

Product 1

HCID 58573628HCID 58573628, compound

Reagents, catalysts & solvents 1

HCID 6344DichloromethaneSolvent

Procedure

To a 0° C. solution of iodine (1.094 g, 4.31 mmol) and imidazole (0.294 g, 4.31 mmol) in dichloromethane (10.27 ml) was added portionwise triphenylphosphine (1.131 g, 4.31 mmol). After 20 min of stirring, (6-methoxypyridin-2-yl)methanol (Adesis, New Castle, Del., 0.5 g, 3.59 mmol) was added to the solution. The reaction was allowed to stir for 1 h at 0° C., quenched with water (50 mL) and extracted with Et2O. The combined organics were dried over MgSO4, and concentrated in vacuo. Silica gel chromatography (gradient elution 1 to 5% Et2O in pentane) afforded 2-(iodomethyl)-6-methoxypyridine. 1H NMR (500 MHz, CHLOROFORM-d) δ ppm 7.49 (dd, J=7.3, 8.3 Hz, 1H), 6.96 (d, J=7.1 Hz, 1H), 6.61 (d, J=8.1 Hz, 1H), 4.44 (s, 2H), 3.94 (s, 3H). Mass Spectrum (ESI) m/z=249.9 (M+1).

Workup

  1. stirringto stir for 1 h at 0° C.
  2. customquenched with water (50 mL)
  3. extractionextracted with Et2O
  4. dry with materialThe combined organics were dried over MgSO4
  5. concentrationconcentrated in vacuo
  6. washSilica gel chromatography (gradient elution 1 to 5% Et2O in pentane)

Sources & evidence

ORD record
ord-43a0824cab25454f9945602f0f1efeec
Source dataset
uspto-grants-2013_10
Patent number
US08569341B2

Reaction notes

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