Methyl iodide → HCID 68815178、化合物

HRID 732463ノート

反応式

HRID 732463 の反応式
[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])[N:7]=[C:6]([NH:15][S:16]([CH3:19])(=[O:18])=[O:17])[CH:5]=1.IC.[C:23](=O)([O-])[O-].[K+].[K+]>CN(C=O)C.[Br-].C([N+](CCCC)(CCCC)CCCC)CCC.C(OCC)(=O)C>[CH3:1][O:2][C:3](=[O:20])[C:4]1[CH:9]=[C:8]([N:10]([CH3:14])[CH2:11][CH2:12][CH3:13])[N:7]=[C:6]([N:15]([S:16]([CH3:19])(=[O:18])=[O:17])[CH3:23])[CH:5]=1

参加物

7

反応物 3

HCID 6328Methyl iodideHCID 11430Potassium CarbonateHCID 68814746HCID 68814746、化合物

生成物 1

HCID 68815178HCID 68815178、化合物収率 87.3%

試薬・触媒・溶媒 3

HCID 74236Tetrabutylammonium Bromide触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

実験手順

Dissolve 2-methanesulfonylamino-6-(methylpropylamino)-isonicotinic acid methyl ester (87 mg, 2.89 mmol) and iodomethane (0.27 mL, 4.33 mmoles) in DMF (10 mL). Add potassium carbonate (639 mg, 4.62 mmol) and tetrabutylammonium bromide (93 mg, 0.98 mmol) and stir at room temperature 1 h. Dilute with ethyl acetate (80 mL), wash with 10% aqueous potassium carbonate (2×15 mL), 0.1 N citric acid (2×15 mL), 1 N lithium chloride (2×15 mL) and saturated aqueous sodium chloride (15 mL). Concentrate organic layer and purify (silica gel chromatography, eluting with 10:90 to 40:60 ethyl acetate:hexanes to give the title compound (796 mg, 87%).

後処理

  1. washwash with 10% aqueous potassium carbonate (2×15 mL), 0.1 N citric acid (2×15 mL), 1 N lithium chloride (2×15 mL) and saturated aqueous sodium chloride (15 mL)
  2. customConcentrate organic layer and purify (silica gel chromatography
  3. washeluting with 10:90 to 40:60 ethyl acetate

出典と根拠

ORDレコード
ord-bc8171f004c74e3390b07f6599b24477
出典データセット
uspto-grants-2009_09
特許番号
US07585885B2

反応ノート

読み込み中…