Tri-o-tolylphosphine → (E)-N-Methyl-N-(1-methyl-1H-indol-2-ylmethyl)-3-[6-(phenylamino)pyridin-3-yl]acrylamide

HRID 225943ノート

反応式

HRID 225943 の反応式
[CH3:1][N:2]([CH2:7][C:8]1[N:9]([CH3:17])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3](=[O:6])[CH:4]=[CH2:5].[C:18]1([NH:24][C:25]2[CH:30]=[CH:29][C:28](Br)=[CH:27][N:26]=2)[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=1.CCN(C(C)C)C(C)C.CC1C=CC=CC=1P(C1C=CC=CC=1C)C1C=CC=CC=1C>C(#N)CC.CC([O-])=O.CC([O-])=O.[Pd+2]>[CH3:1][N:2]([CH2:7][C:8]1[N:9]([CH3:17])[C:10]2[C:15]([CH:16]=1)=[CH:14][CH:13]=[CH:12][CH:11]=2)[C:3](=[O:6])/[CH:4]=[CH:5]/[C:28]1[CH:27]=[N:26][C:25]([NH:24][C:18]2[CH:23]=[CH:22][CH:21]=[CH:20][CH:19]=2)=[CH:30][CH:29]=1

参加物

7

反応物 4

HCID 80271Tri-o-tolylphosphineHCID 81531DiisopropylethylamineHCID 133140415-bromo-N-phenylpyridin-2-amineHCID 20752825N-Methyl-N-[(1-methyl-2-indolyl)methyl]acrylamide

生成物 1

HCID 60208936(E)-N-Methyl-N-(1-methyl-1H-indol-2-ylmethyl)-3-[6-(phenylamino)pyridin-3-yl]acrylamide収率 69%

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 7854Propionitrile溶媒

実験手順

N-Methyl-N-(1-methyl-1H-indol-2-ylmethyl)acrylamide (from Example 76(a)) was taken up in propionitrile (50 mL). To this solution was added with stirring 2-phenylamino-5-bromopyridine (1.3 g, 5.2 mmole), DIEA (1.8 mL, 10 mmole), Pd(OAc)2 (112 mg, 0.5 mmole) and P(o-tol)3 (304 mg, 1.0 mmole). The reaction was purged with argon then stirred at reflux for 16 h. After cooling to room temperature the reaction was concentrated to dryness under vacuum. Flash chromatography on silica gel (5% methanol/CHCl3) followed by a second flash column on silica gel (50-70% EtOAc/CHCl3) left a residue that was triturated with EtOAc/petroleum ether. Filtration and drying under vacuum gave the title compound (1.42 g, 69%) as an off-white powder: MS (ES) m/e 396.20 (M+H)+.

後処理

  1. customThe reaction was purged with argon
  2. temperatureat reflux for 16 h
  3. concentrationwas concentrated to dryness under vacuum
  4. waitleft a residue that
  5. customwas triturated with EtOAc/petroleum ether
  6. filtrationFiltration
  7. customdrying under vacuum

出典と根拠

ORDレコード
ord-c897d192d75d4e1e942d73071bb3f0c3
出典データセット
uspto-grants-2009_07
特許番号
US07557125B2

反応ノート

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