Trimethylsilyldiazomethane → Methyl 4-iodo-2-methoxynicotinate

HRID 1034935

Reaction equation

HRID 1034935 reaction equation
[I:1][C:2]1[C:7]([C:8]([OH:10])=[O:9])=[C:6]([O:11][CH3:12])[N:5]=[CH:4][CH:3]=1.[CH3:13][Si](C=[N+]=[N-])(C)C>CO>[I:1][C:2]1[C:7]([C:8]([O:10][CH3:13])=[O:9])=[C:6]([O:11][CH3:12])[N:5]=[CH:4][CH:3]=1

Participants

4

Reactant 2

HCID 167693TrimethylsilyldiazomethaneHCID 184399404-Iodo-2-methoxypyridine-3-carboxylic acid

Product 1

HCID 58819970Methyl 4-iodo-2-methoxynicotinate

Reagents, catalysts & solvents 1

HCID 887MethanolSolvent

Conditions

Temperature
0 °C

Procedure

4-Iodo-2-methoxynicotinic acid (800 mg, 2.87 mmol) is dissolved in MeOH (7 mL) and cooled at 0° C. Trimethylsilyldiazomethane (9 mL, 2M in hexane, 4.5 mmol) is added slowly over 20 minutes. The reaction mixture is brought to room temperature and stirred for 16 hours. The reaction mixture is concentrated and purified by silica gel column chromatography using hexane:ethyl acetate as eluent to afford the desired compound. 1H NMR 400 MHz (DMSO-d6) δ 7.88 (d, 1H, J=5.6 Hz), 7.34 (d, 1H, J=5.6 Hz), 4.12 (s, 3H), 3.84 (s, 1H); MS m/z 294.1 (M+1).

Workup

  1. customis brought to room temperature
  2. concentrationThe reaction mixture is concentrated
  3. custompurified by silica gel column chromatography

Sources & evidence

ORD record
ord-38bdaf2c97254d0e88dda5193b8834be
Source dataset
uspto-grants-2013_10
Patent number
US08546370B2

Linked notes

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