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

HRID 530032노트

반응식

HRID 530032 반응식
[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

참가 물질

7

반응물 4

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

생성물 1

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

시약·촉매·용매 2

HCID 167845palladium(II) acetate촉매HCID 8028Tetrahydrofuran용매

반응 조건

온도
100 °C

실험 절차

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.

후처리

  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)

출처 및 근거

ORD 기록
ord-d627c17449db46f8acb10a2d0803dcae
출처 데이터셋
uspto-grants-2016_05
특허 번호
US09351973B2

반응 노트

불러오는 중…