(2,4-Dichlorophenoxy)Acetic Acid → HCID 24812094、化合物

HRID 1945431ノート

反応式

HRID 1945431 の反応式
[Cl:1][C:2]1[CH:12]=[C:11]([Cl:13])[CH:10]=[CH:9][C:3]=1[O:4][CH2:5][C:6]([OH:8])=O.[CH3:14][O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([NH2:23])[CH:18]=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>[CH3:14][O:15][C:16](=[O:24])[C:17]1[CH:22]=[CH:21][N:20]=[C:19]([NH:23][C:6](=[O:8])[CH2:5][O:4][C:3]2[CH:9]=[CH:10][C:11]([Cl:13])=[CH:12][C:2]=2[Cl:1])[CH:18]=1

参加物

7

反応物 4

HCID 1486(2,4-Dichlorophenoxy)Acetic AcidHCID 8857Ethyl AcetateHCID 236984Methyl 2-aminopyridine-4-carboxylateHCID 2724699PyBOP

生成物 1

HCID 24812094HCID 24812094、化合物収率 71.6%

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-dichloro-phenoxyacetic acid (0.200 g, 0.9 mmol), 2-amino isonicotinic acid methyl ester (207 mg, 1.36 mmol) and DMAP (0.222 g, 1.81 mmol) in DMF 13 mL was added PyBOP (946 mg, 1.81 mmol) at room temperature. Reaction mixture was stirred 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=1:9-4:6) to give 2-[2-(2,4-dichloro-phenoxy)-acetylamino]-isonicotinic acid methyl ester as a colorless solid (0.229 g, 71% yield).

後処理

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

出典と根拠

ORDレコード
ord-509c1ac13b76441099cb11a0c0b359e9
出典データセット
uspto-grants-2013_03
特許番号
US08394799B2

反応ノート

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