Diisopropylethylamine → Methyl 6-amino-5-((3-(3-methylfuran-2-carboxamido)phenyl)ethynyl)nicotinate

HRID 391589ノート

反応式

HRID 391589 の反応式
[C:1]([C:3]1[CH:4]=[C:5]([NH:9][C:10]([C:12]2[O:13][CH:14]=[CH:15][C:16]=2[CH3:17])=[O:11])[CH:6]=[CH:7][CH:8]=1)#[CH:2].[NH2:18][C:19]1[C:28](I)=[CH:27][C:22]([C:23]([O:25][CH3:26])=[O:24])=[CH:21][N:20]=1.CCN(C(C)C)C(C)C>CN(C=O)C.CCOC(C)=O.Cl[Pd](Cl)([P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1)[P](C1C=CC=CC=1)(C1C=CC=CC=1)C1C=CC=CC=1.[Cu]I>[CH3:26][O:25][C:23](=[O:24])[C:22]1[CH:27]=[C:28]([C:2]#[C:1][C:3]2[CH:8]=[CH:7][CH:6]=[C:5]([NH:9][C:10]([C:12]3[O:13][CH:14]=[CH:15][C:16]=3[CH3:17])=[O:11])[CH:4]=2)[C:19]([NH2:18])=[N:20][CH:21]=1

参加物

8

反応物 3

HCID 81531DiisopropylethylamineHCID 15350913Methyl 6-amino-5-iodopyridine-3-carboxylateHCID 51337833N-(3-ethynylphenyl)-3-methylfuran-2-carboxamide

生成物 1

HCID 57657938Methyl 6-amino-5-((3-(3-methylfuran-2-carboxamido)phenyl)ethynyl)nicotinate収率 82%

試薬・触媒・溶媒 4

HCID 24350Copper(1+) iodide; Copper(I) iodide; Cuprous iodide; Cuprous iodide (CuI)触媒HCID 178418476HCID 178418476、化合物触媒HCID 6228Dimethylformamide溶媒HCID 8857Ethyl Acetate溶媒

反応条件

温度
50 °C

実験手順

In a 4 mL vial, N-(3-ethynylphenyl)-3-methylfuran-2-carboxamide (0.607 g, 2.70 mmol) and methyl 6-amino-5-iodonicotinate (0.5 g, 1.80 mmol) were dissolved in DMF (6 mL) The solution was degassed by bubbling N2(g) through it for ˜30 min. To the degassed solution was added DIPEA (1.25 mL, 7.19 mmol), followed by Pd(PPh3)2Cl2 (0.126 g, 0.18 mmol) and CuI (0.068 g, 0.360 mmol). The reaction mixture was allowed to stir at 50° C. for 3 h. The reaction mixture then was taken up in EtOAc (10 mL) and was extracted with brine (3×10 mL). The organic layers were combined and concentrated in vacuo. The crude mixture was purified via column chromatography (gradient eluant mixture of EtOAc in Hexanes: 25% to 100% EtOAc) to give the title compound as a white solid (0.554 g, 82%).

後処理

  1. customwas degassed
  2. customby bubbling N2(g) through it for ˜30 min
  3. extractionwas extracted with brine (3×10 mL)
  4. concentrationconcentrated in vacuo
  5. customThe crude mixture was purified via column chromatography (gradient eluant mixture of EtOAc in Hexanes: 25% to 100% EtOAc)

出典と根拠

ORDレコード
ord-e3c46647a9db499b8887af1df3e2a169
出典データセット
uspto-grants-2013_02
特許番号
US08383825B2

反応ノート

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