Phenylsilane → Methyl 4-([2,3']bipyridinyl-6-ylaminomethyl)-benzoate

HRID 852902ノート

反応式

HRID 852902 の反応式
[N:1]1[C:6]([NH2:7])=[CH:5][CH:4]=[CH:3][C:2]=1[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1.[CH:14]([C:16]1[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=1)=O.C1([SiH3])C=CC=CC=1>C1COCC1.C([Sn](Cl)(Cl)CCCC)CCC>[N:1]1[C:6]([NH:7][CH2:14][C:16]2[CH:25]=[CH:24][C:19]([C:20]([O:22][CH3:23])=[O:21])=[CH:18][CH:17]=2)=[CH:5][CH:4]=[CH:3][C:2]=1[C:8]1[CH:9]=[N:10][CH:11]=[CH:12][CH:13]=1

参加物

6

反応物 3

HCID 12752PhenylsilaneHCID 15294Methyl 4-FormylbenzoateHCID 11586359[2,3'-Bipyridin]-6-amine

生成物 1

HCID 58930610Methyl 4-([2,3']bipyridinyl-6-ylaminomethyl)-benzoate収率 98.3%

試薬・触媒・溶媒 2

HCID 12688Dibutyltin dichloride触媒HCID 8028Tetrahydrofuran溶媒

実験手順

To a stirred suspension of a mixture of 11 (3.00 g, 17.52 mmol), methyl 4-formylbenzoate (4.62 g, 28.11 mmol, 1.5-2.0 equiv.) and dibutyl tin dichloride 160 mg, 0.53 mmol) in anhydrous THF (15 mL) at room temperature was added phenylsilane (2.34 mL, 19.28 mmol) in three portions over two days. After stirring for 2 to 7 days the reaction mixture was filtered, filtrate was concentrated and purified by flash chromatography on silica gel (MeOH/CH2Cl2, 2/98→10/90) to afford the title compound 12 (5.50 g, 17.22 mmol, 98% yield) as a pale yellow solid. 1H NMR (400 MHz, DMSO-d6) δ (ppm): 9.11 (dd, J=2.3, 0.7 Hz, 1H), 8.55 (dd, J=4.7, 1.8 Hz, 1H), 8.29-8.24 (m, 1H), 7.93 (d, J=8.4 Hz, 2H), 7.57-7.40 (m, 5H), 7.18 (d, J=7.2 Hz, 1H), 6.59 (d, J=8.2 Hz 1H), 4.69 (d, J=6.1 Hz, 2H), 3.85 (s, 3H).

後処理

  1. filtrationwas filtered
  2. concentrationfiltrate was concentrated
  3. custompurified by flash chromatography on silica gel (MeOH/CH2Cl2, 2/98→10/90)

出典と根拠

ORDレコード
ord-cdbb4155d2954433adc05ef0eed4ec93
出典データセット
uspto-grants-2007_08
特許番号
US07253204B2

反応ノート

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