Lithium diisopropylamide → (+/-)-1-[1-(6-chloropyridin-2-yl)-2,2-dipyridin-3-ylethyl]pyridin-2(1H)-one

HRID 1360130노트

반응식

HRID 1360130 반응식
[Cl:1][C:2]1[N:7]=[C:6]([CH2:8][N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]2=[O:15])[CH:5]=[CH:4][CH:3]=1.[Li+].CC([N-]C(C)C)C.Cl[CH:25]([C:32]1[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=1)[C:26]1[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=1>C1COCC1>[Cl:1][C:2]1[N:7]=[C:6]([CH:8]([N:9]2[CH:14]=[CH:13][CH:12]=[CH:11][C:10]2=[O:15])[CH:25]([C:32]2[CH:33]=[N:34][CH:35]=[CH:36][CH:37]=2)[C:26]2[CH:27]=[N:28][CH:29]=[CH:30][CH:31]=2)[CH:5]=[CH:4][CH:3]=1

참가 물질

5

반응물 3

HCID 2724682Lithium diisopropylamideHCID 574257801-[(6-chloropyridin-2-yl)methyl]pyridin-2(1H)-oneHCID 574257823,3'-(Chloromethylene)dipyridine

생성물 1

HCID 59706213(+/-)-1-[1-(6-chloropyridin-2-yl)-2,2-dipyridin-3-ylethyl]pyridin-2(1H)-one

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매2회

반응 조건

온도
-78 °C

실험 절차

To the solution of 1-[(6-chloropyridin-2-yl)methyl]pyridin-2(1H)-one (0.3 g, 1.36 mmol) in THF (6 mL) at −78° C. was added LDA(0.83 mL, 1.8 M) and stirred at −78° C. for 1 h. The solution of 3-[chloro(pyridin-3-yl)methyl]pyridine (0.278 g, 1.36 mmol) in THF (3 mL) was added and the mixture was warmed to 0° C. and stirred at 0° C. for 1 h. The reaction was quenched with water and extracted with CH2Cl2. The combined organic layer was dried, filtered, and concentrated. The residue was purified by silica gel chromatography (3% MeOH in CH2Cl2) to give (±)-1-[1-(6-chloropyridin-2-yl)-2,2-dipyridin-3-ylethyl]pyridin-2(1H)-one. 1H-NMR (500 MHz, CDCl3) δ 8.58 (d, 1H, J=2.2), 8.53 (d, 1H, J=2.0), 8.42 (dd, 1H, J=4.6, 1.2), 8.35 (dd, 1H, J=4.6, 1.2), 7.92 (d, 1H, 3=6.6), 7.84 (d, 1H, J=8.0), 7.64 (d, 1H, J=8.0), 7.48 (t, 1H, J=7.7), 7.25-7.09 (m, 6H), 6.41 (d, 1H, J=9.0), 6.09 (t, 1H, J=6.7), 5.30 (d, 1H, J=12.2). LRMS m/z (M+H) Calcd: 389.8. found: 389.0.

후처리

  1. temperaturethe mixture was warmed to 0° C.
  2. stirringstirred at 0° C. for 1 h
  3. customThe reaction was quenched with water
  4. extractionextracted with CH2Cl2
  5. customThe combined organic layer was dried
  6. filtrationfiltered
  7. concentrationconcentrated
  8. customThe residue was purified by silica gel chromatography (3% MeOH in CH2Cl2)

출처 및 근거

ORD 기록
ord-3973c8fd5d6e460091391ec1c77f5d0d
출처 데이터셋
uspto-grants-2011_02
특허 번호
US07879839B2

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