2-Chloronicotinonitrile → 2-(1-Methyl-1H-indazol-5-yloxy)-nicotinonitrile

HRID 909141

반응식

HRID 909141 반응식
[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([OH:11])=[CH:8][CH:9]=2)[CH:4]=[N:3]1.Cl[C:13]1[N:20]=[CH:19][CH:18]=[CH:17][C:14]=1[C:15]#[N:16]>CS(C)=O.O>[CH3:1][N:2]1[C:10]2[C:5](=[CH:6][C:7]([O:11][C:13]3[N:20]=[CH:19][CH:18]=[CH:17][C:14]=3[C:15]#[N:16])=[CH:8][CH:9]=2)[CH:4]=[N:3]1

참가 물질

5

반응물 2

HCID 810792-ChloronicotinonitrileHCID 441192401-Methyl-1H-indazol-5-ol

생성물 1

HCID 574187422-(1-Methyl-1H-indazol-5-yloxy)-nicotinonitrile수율 90%

시약·촉매·용매 2

HCID 679Dimethyl Sulfoxide용매HCID 962Water용매

반응 조건

온도
110 °C

실험 절차

1-Methyl-1H-indazol-5-ol (in) (synthesized as described in Example 94) (0.10 g, 0.68 mmol) and 2-chloro-nicotinonitrile (2n) (0.11 g, 0.81 mmol) were suspended in DMSO (2 mL). The reaction mixture was heated to 110° C. for 18 hours. The reaction mixture was diluted with water and extracted into EtOAc. The combined organics were dried, Na2SO4 and concentrated under reduced pressure to afford the crude product. Purification by flash column chromatography (20-100% EtOAc/Hexanes) furnished the desired product (3n), (0.152 g, 90% yield). 1H NMR (400 mHz, CD3OD) δ 8.27-8.25 (m, 1H), 8.23-8.20 (m, 1H), 8.01 (s, 1H), 7.62 (d, J=8.6 Hz, 1H), 7.57 (d, J=2.3 Hz, 1H), 7.28-7.26 (m, 1H), 7.23-7.20 (m, 1H), 4.10 (s, 3H); MS (ESI+) m/z 251 (M+H) detected.

후처리

  1. extractionextracted into EtOAc
  2. customThe combined organics were dried
  3. concentrationNa2SO4 and concentrated under reduced pressure
  4. customto afford the crude product
  5. customPurification by flash column chromatography (20-100% EtOAc/Hexanes)

출처 및 근거

ORD 기록
ord-527f16d5580545d8a53207bffcce1909
출처 데이터셋
uspto-grants-2011_09
특허 번호
US08017641B2

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