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

HRID 416215노트

반응식

HRID 416215 반응식
[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

참가 물질

6

반응물 3

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

생성물 1

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

시약·촉매·용매 2

HCID 12688Dibutyltin dichloride촉매HCID 8028Tetrahydrofuran용매

실험 절차

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).

후처리

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

출처 및 근거

ORD 기록
ord-f91cd367ada84cbaa55ac548f8b3d3a4
출처 데이터셋
uspto-grants-2012_01
특허 번호
US08088805B2

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