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

HRID 1715562

反応式

HRID 1715562 の反応式
[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

参加物

5

反応物 2

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

生成物 1

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

試薬・触媒・溶媒 2

HCID 679Dimethyl Sulfoxide溶媒HCID 962Water溶媒

反応条件

温度
110 °C

実験手順

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.

後処理

  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)

出典と根拠

ORDレコード
ord-c6f15d5d71fd456e8d896751e57adc56
出典データセット
uspto-grants-2010_09
特許番号
US07799782B2

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