Water → (2-(3-(Benzyloxy)-6-chloropyridin-2-yl)pyrazolo[1,5-a]pyridin-3-yl)methanol

HRID 1776899노트

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HRID 1776899 반응식
[CH2:1]([O:8][C:9]1[C:10]([C:16]#[C:17][CH2:18][OH:19])=[N:11][C:12]([Cl:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[I-].[NH2:21][N+:22]1[CH:27]=[CH:26][CH:25]=[CH:24][CH:23]=1.C1CCN2C(=NCCC2)CC1.O>CC#N>[CH2:1]([O:8][C:9]1[C:10]([C:16]2[C:17]([CH2:18][OH:19])=[C:23]3[CH:24]=[CH:25][CH:26]=[CH:27][N:22]3[N:21]=2)=[N:11][C:12]([Cl:15])=[CH:13][CH:14]=1)[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

참가 물질

6

반응물 4

HCID 962WaterHCID 811841,8-Diazabicyclo(5.4.0)undec-7-eneHCID 2733704Pyridinium, 1-amino-, iodide (1:1)HCID 867282833-(3-(Benzyloxy)-6-chloropyridin-2-yl)prop-2-yn-1-ol

생성물 1

HCID 86728284(2-(3-(Benzyloxy)-6-chloropyridin-2-yl)pyrazolo[1,5-a]pyridin-3-yl)methanol수율 47.5%

시약·촉매·용매 1

HCID 6342Acetonitrile용매

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온도
80 °C

실험 절차

A mixture of compound 3-(3-(benzyloxy)-6-chloropyridin-2-yl)prop-2-yn-1-ol (1.9 g, 6.9 mmol), 1-aminopyridinium iodide (2.3 g, 10.4 mmol) and DBU (2.2 g, 14 mmol) in MeCN (15 mL) was stirred at 80° C. for 2 hours. Water (15 mL) was added and the mixture was extracted with ethyl acetate. The organic layer was washed with brine and dried over Na2SO4. After concentrated, the resulting residue was purified using column chromatography (petroleum ether:ethyl acetate=1:1) to provide the product of compound (2-(3-(benzyloxy)-6-chloropyridin-2-yl)pyrazolo[1,5-a]pyridin-3-yl)methanol (1.2 g, yield: 47%). 1H-NMR (CDCl3, 400 MHz) δ 8.42 (d, J=8.0 Hz, 1H), 7.58 (d, J=8.0 Hz, 1H), 7.37 (d, J=8.0 Hz, 1H), 7.29˜7.22 (m, 3H), 7.21˜7.17 (m, 3H), 7.02 (t, J=8.0 Hz, 1H), 6.76 (dt, J=1.6, 8.0 Hz, 1H), 5.09 (s, 2H), 4.77 (d, J=6.4 Hz, 2H). MS (M+H)+: 366/368.

후처리

  1. extractionthe mixture was extracted with ethyl acetate
  2. washThe organic layer was washed with brine
  3. dry with materialdried over Na2SO4
  4. concentrationAfter concentrated
  5. customthe resulting residue was purified

출처 및 근거

ORD 기록
ord-2bb5ea1660db457b8d0a60b4efec4b75
출처 데이터셋
uspto-grants-2016_02
특허 번호
US09265773B2

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