Trichlorophenoxyacetic acid → 2-[2-(2,4,5-Trichloro-phenoxy)-acetylamino]-isonicotinic acid methyl ester

HRID 1945432

反応式

HRID 1945432 の反応式
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[C:10]([Cl:14])=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.[CH3:15][O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][N:21]=[C:20]([NH2:24])[CH:19]=1.C1CN([P+](ON2N=NC3C=CC=CC2=3)(N2CCCC2)N2CCCC2)CC1.F[P-](F)(F)(F)(F)F.C(OCC)(=O)C>CN(C1C=CN=CC=1)C.CN(C=O)C>[CH3:15][O:16][C:17](=[O:25])[C:18]1[CH:23]=[CH:22][N:21]=[C:20]([NH:24][C:6](=[O:8])[CH2:5][O:4][C:3]2[CH:9]=[C:10]([Cl:14])[C:11]([Cl:13])=[CH:12][C:2]=2[Cl:1])[CH:19]=1

参加物

7

反応物 4

HCID 1480Trichlorophenoxyacetic acidHCID 8857Ethyl AcetateHCID 236984Methyl 2-aminopyridine-4-carboxylateHCID 2724699PyBOP

生成物 1

HCID 248120952-[2-(2,4,5-Trichloro-phenoxy)-acetylamino]-isonicotinic acid methyl ester収率 24.45%

試薬・触媒・溶媒 2

HCID 142844-(Dimethylamino)pyridine触媒HCID 6228Dimethylformamide溶媒

実験手順

To solution of (2,4,5-trichloro-phenoxy)-acetic acid (150 mg, 0.59 mmol), 2-amino isonicotinic acid methyl ester (179 mg, 1.18 mmol) and DMAP (144 mg, 1.18 mmol) in DMF 13 mL was added PyBOP (614 mg, 1.18 mmol) at room temperature. Reaction mixture was stared at room temperature. Resulting mixture poured onto ice cold water, was diluted by ethyl acetate. The organic phase was separated, sequentially washed with aqueous sodium bicarbonate, brine and water, dried over anhydrous MgSO4, and concentrated. The residue was purified by flash silica gel column chromatography (EtoAC:Hexane=1:1) to give 2-[2-(2,4,5-trichloro-phenoxy)-acetylamino]-isonicotinic acid methyl ester as a colorless solid (0.056 g, 24.45% yield).

後処理

  1. customReaction mixture
  2. customwas stared at room temperature
  3. customResulting mixture
  4. additionpoured onto ice cold water
  5. customThe organic phase was separated
  6. washsequentially washed with aqueous sodium bicarbonate, brine and water
  7. dry with materialdried over anhydrous MgSO4
  8. concentrationconcentrated
  9. customThe residue was purified by flash silica gel column chromatography (EtoAC:Hexane=1:1)

出典と根拠

ORDレコード
ord-dd5790bf973b45f2954d627f426d14e2
出典データセット
uspto-grants-2013_03
特許番号
US08394799B2

関連ノート

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