Trimethylsilyldiazomethane → Methyl 4-iodo-2-methoxynicotinate

HRID 1034935

반응식

HRID 1034935 반응식
[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

참가 물질

4

반응물 2

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

생성물 1

HCID 58819970Methyl 4-iodo-2-methoxynicotinate

시약·촉매·용매 1

HCID 887Methanol용매

반응 조건

온도
0 °C

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-38bdaf2c97254d0e88dda5193b8834be
출처 데이터셋
uspto-grants-2013_10
특허 번호
US08546370B2

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