Cesium carbonate → 2-Chloro-3-cyclopropylpyrazolo[1,5-A]pyridine

HRID 530032ノート

反応式

HRID 530032 の反応式
[Cl:1][C:2]1[C:10](I)=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1.[CH:12]1(B(O)O)[CH2:14][CH2:13]1.C(=O)([O-])[O-].[Cs+].[Cs+].C1(P(C2C=CC=CC=2)C2C=CC=CC=2)C=CC=CC=1>O1CCCC1.C([O-])(=O)C.[Pd+2].C([O-])(=O)C>[Cl:1][C:2]1[C:10]([CH:12]2[CH2:14][CH2:13]2)=[C:5]2[CH:6]=[CH:7][CH:8]=[CH:9][N:4]2[N:3]=1

参加物

7

反応物 4

HCID 10796Cesium carbonateHCID 11776TriphenylphosphineHCID 2760897Cyclopropylboronic acidHCID 717433402-Chloro-3-iodopyrazolo[1,5-A]pyridine

生成物 1

HCID 717433392-Chloro-3-cyclopropylpyrazolo[1,5-A]pyridine

試薬・触媒・溶媒 2

HCID 167845palladium(II) acetate触媒HCID 8028Tetrahydrofuran溶媒

反応条件

温度
100 °C

実験手順

A mixture 2-chloro-3-iodopyrazolo-[1,5-a]pyridine (27-3; 0.7 g, 2.52 mmol), cyclopropyl boronic acid (0.43 g, 5.036 mmol), and cesium carbonate (2.46 g, 7.56 mmol), in tetrahydrofuran (15.0 mL) was degassed for 10 min. Then triphenylphosphine (0.132 g, 0.504 mmol) and palladium acetate (0.056 g, 0.252 mmol) were added and heated in a sealed tube at 100° C. for 18 h. The reaction mixture was then cooled to room temperature, filtered and concentrated under reduced pressure. Purification of the resulting residue by flash chromatography on silica gel (0-5% ethyl acetate in hexanes) provided 2-chloro-3-cyclopropylpyrazolo[1,5-a]pyridine. 1H NMR (400 MHz, CDCl3) δ 8.29-8.27 (d, J=7.2 Hz, 1 H), 7.50-7.48 (d, J=8.8 Hz, 1 H), 7.11-7.07 (t, J=7.8 Hz, 1 H), 6.72-6.69 (m, 1 H), 1.80-1.73 (m, 1 H), 0.98-0.95 (m, 2 H), 0.75-0.73 (m, 2 H). MS (M+1): 139.1.

後処理

  1. temperatureThe reaction mixture was then cooled to room temperature
  2. filtrationfiltered
  3. concentrationconcentrated under reduced pressure
  4. customPurification of the resulting residue by flash chromatography on silica gel (0-5% ethyl acetate in hexanes)

出典と根拠

ORDレコード
ord-d627c17449db46f8acb10a2d0803dcae
出典データセット
uspto-grants-2016_05
特許番号
US09351973B2

反応ノート

読み込み中…