Sodium hydride → 6-[2-(2-Chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-ylamino]isonicotinonitrile

HRID 626678ノート

反応式

HRID 626678 の反応式
[H-].[Na+].[NH2:3][C:4]1[CH:9]=[C:8]([C:10]#[N:11])[CH:7]=[CH:6][N:5]=1.Cl[C:13]1[C:18]2=[CH:19][N:20]([C:22]3[C:27]([F:28])=[CH:26][CH:25]=[CH:24][C:23]=3[Cl:29])[N:21]=[C:17]2[CH:16]=[CH:15][N:14]=1>CN(C=O)C>[Cl:29][C:23]1[CH:24]=[CH:25][CH:26]=[C:27]([F:28])[C:22]=1[N:20]1[CH:19]=[C:18]2[C:13]([NH:3][C:4]3[N:5]=[CH:6][CH:7]=[C:8]([CH:9]=3)[C:10]#[N:11])=[N:14][CH:15]=[CH:16][C:17]2=[N:21]1

参加物

5

反応物 3

HCID 24758Sodium hydrideHCID 70155242-AminoisonicotinonitrileHCID 866970434-Chloro-2-(2-chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine

生成物 1

HCID 696713726-[2-(2-Chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridin-4-ylamino]isonicotinonitrile収率 10.2%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

実験手順

Sodium hydride (12 mg, 0.30 mmol) was added to a solution of 2-amino-4-cyanopyridine (36 mg, 0.30 mmol) in DMF (2 mL) in a microwave vial and stirred for 5 minutes. 4-Chloro-2-(2-chloro-6-fluorophenyl)-2H-pyrazolo[4,3-c]pyridine (76 mg, 0.27 mmol) was added and then the vial was sealed, purged with nitrogen and irradiated at 150° C. for 10 minutes in the microwave. The reaction mixture was cooled and partitioned between ethyl acetate and water. The organic layer was washed with brine, dried over anhydrous sodium sulfate, and concentrated under reduced pressure. The residue was purified by silica gel flash chromatography (50% ethyl acetate in cyclohexane) to afford the title compound as a yellow solid (10 mg, 10% yield). 1H NMR (400 MHz, DMSO-d6): δ 9.61 (s, 1H), 8.77 (dd, J=5.2, 0.9 Hz, 1H), 7.99 (d, J=7.3 Hz, 1H), 7.85 (s, 1H), 7.81-7.80 (m, 2H), 7.73 (d, J=8.2 Hz, 1H), 7.67 (t, J=9.0 Hz, 1H), 7.58 (dd, J=7.3, 0.9 Hz, 1H). LCMS (Method B): RT=2.98 min, m/z: 365 [M+H+].

後処理

  1. customthe vial was sealed
  2. custompurged with nitrogen
  3. customirradiated at 150° C. for 10 minutes in the microwave
  4. temperatureThe reaction mixture was cooled
  5. custompartitioned between ethyl acetate and water
  6. washThe organic layer was washed with brine
  7. dry with materialdried over anhydrous sodium sulfate
  8. concentrationconcentrated under reduced pressure
  9. customThe residue was purified by silica gel flash chromatography (50% ethyl acetate in cyclohexane)

出典と根拠

ORDレコード
ord-d1ed04d3124b43d088e7618fc1b2a1b2
出典データセット
uspto-grants-2016_04
特許番号
US09309240B2

反応ノート

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