Trimethylsilyldiazomethane → Methyl 4-iodo-2-methoxynicotinate

HRID 1034935

反応式

HRID 1034935 の反応式
[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

参加物

4

反応物 2

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

生成物 1

HCID 58819970Methyl 4-iodo-2-methoxynicotinate

試薬・触媒・溶媒 1

HCID 887Methanol溶媒

反応条件

温度
0 °C

実験手順

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).

後処理

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

出典と根拠

ORDレコード
ord-38bdaf2c97254d0e88dda5193b8834be
出典データセット
uspto-grants-2013_10
特許番号
US08546370B2

関連ノート

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