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

HRID 1776899ノート

反応式

HRID 1776899 の反応式
[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

参加物

6

反応物 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

生成物 1

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

試薬・触媒・溶媒 1

HCID 6342Acetonitrile溶媒

反応条件

温度
80 °C

実験手順

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.

後処理

  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

出典と根拠

ORDレコード
ord-2bb5ea1660db457b8d0a60b4efec4b75
出典データセット
uspto-grants-2016_02
特許番号
US09265773B2

反応ノート

読み込み中…