4-Iodo-o-toluidine → 3-[(2-Methyl-4-iodophenyl)amino]isonicotinic acid

HRID 78762

反応式

HRID 78762 の反応式
[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH2:6])=[C:4]([CH3:9])[CH:3]=1.F[C:11]1[CH:12]=[N:13][CH:14]=[CH:15][C:16]=1[C:17]([OH:19])=[O:18].[Li+].C[Si]([N-][Si](C)(C)C)(C)C>C1COCC1>[I:1][C:2]1[CH:8]=[CH:7][C:5]([NH:6][C:15]2[CH:14]=[N:13][CH:12]=[CH:11][C:16]=2[C:17]([OH:19])=[O:18])=[C:4]([CH3:9])[CH:3]=1

参加物

5

反応物 3

HCID 832214-Iodo-o-toluidineHCID 3453613-Fluoropyridine-4-carboxylic acidHCID 2733832Lithium Hexamethyldisilazide

生成物 1

HCID 576496173-[(2-Methyl-4-iodophenyl)amino]isonicotinic acid収率 59%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
-78 °C

実験手順

4-Iodo-2-methylaniline (233 mg, 1.00 mmol) and 3-fluoropyridine-4-carboxylic acid (141 mg, 1.00 mmol) were dissolved in dry THF (6.0 ml) under argon and the mixture was cooled to −78° C. A solution of LiHMDS (1.0M in THF, 3.5 ml) was added and the reaction mixture was allowed to warm to ambient temperature. After 36 h the reaction was quenched by adding solid NH4Cl. After filtration the volatiles were removed in vacuo and the crude material was purified by flash chromatography using silica gel and a gradient of 0-10% methanol in DCM as eluent to give 208 mg (588 μmol; 59% yield) of pure desired product.

後処理

  1. temperatureto warm to ambient temperature
  2. customAfter 36 h the reaction was quenched
  3. additionby adding solid NH4Cl
  4. filtrationAfter filtration the volatiles
  5. customwere removed in vacuo
  6. customthe crude material was purified by flash chromatography

出典と根拠

ORDレコード
ord-6b959f9988bc47e1879277c867aac7fb
出典データセット
uspto-grants-2014_09
特許番号
US08841459B2

関連ノート

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