Trifluoroacetic acid → 5-(5-fluoropyridin-3-yl)-N-(6-(trifluoromethyl)pyridin-3-yl)-1H-indazole-3-carboxamide

HRID 2367704ノート

反応式

HRID 2367704 の反応式
C(O)(C(F)(F)F)=O.[F:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[N:20](C2CCCCO2)[N:19]=[C:18]3[C:30]([NH:32][C:33]2[CH:34]=[N:35][C:36]([C:39]([F:42])([F:41])[F:40])=[CH:37][CH:38]=2)=[O:31])[CH:12]=[N:13][CH:14]=1.C([SiH](CC)CC)C>C(Cl)Cl>[F:8][C:9]1[CH:10]=[C:11]([C:15]2[CH:16]=[C:17]3[C:21](=[CH:22][CH:23]=2)[NH:20][N:19]=[C:18]3[C:30]([NH:32][C:33]2[CH:34]=[N:35][C:36]([C:39]([F:42])([F:40])[F:41])=[CH:37][CH:38]=2)=[O:31])[CH:12]=[N:13][CH:14]=1

参加物

5

反応物 3

HCID 6422Trifluoroacetic acidHCID 12052TriethylsilaneHCID 866796995-(5-fluoropyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-N-(6-(trifluoromethyl)pyridin-3-yl)-1H-indazole-3-carboxamide

生成物 1

HCID 866797005-(5-fluoropyridin-3-yl)-N-(6-(trifluoromethyl)pyridin-3-yl)-1H-indazole-3-carboxamide収率 21%

試薬・触媒・溶媒 1

HCID 6344Dichloromethane溶媒

実験手順

TFA (10 mL) was added to a solution of 5-(5-fluoropyridin-3-yl)-1-(tetrahydro-2H-pyran-2-yl)-N-(6-(trifluoromethyl)pyridin-3-yl)-1H-indazole-3-carboxamide (CXXX) (0.420 g, 0.86 mmol) and triethylsilane (0.345 mL, 2.16 mmol) in DCM (10 mL) and stirred 5 h at room temperature. The solvent was removed under vacuum. The residue was treated with water, sonicated briefly to disperse the solids, basified to pH 9.0 with 5 N NH4OH and sonicated again. The solids were filtered, washed with cold water and air dried at room temperature. The solids were suspended in DCM:MeOH (1:1) mixture and boiled to get a clear solution. The solution was cooled to room temperature. The solids formed were filtered washed with DCM and dried under vacuum at room temperature to get 5-(5-fluoropyridin-3-yl)-N-(6-(trifluoromethyl)pyridin-3-yl)-1H-indazole-3-carboxamide (2) as a white solid (72.9 mg, 0.18 mmol, 21% yield). 1H NMR (DMSO-d6) δ ppm 14.13 (br. s, 1H), 11.11 (s, 1H), 9.27 (d, J=1.8 Hz, 1H), 8.84 (m, 1H), 8.63 (dd, J=6.8, 1.8 Hz, 1H), 8.60 (d, J=2.0 Hz, 1H), 8.53 (m, 1H), 8.14-8.11 (m, 1H), 7.94 (d, J=6.9 Hz, 1H), 7.90-7.83 (m, 2H); ESIMS found for C19H11F4N5O m/z 402.30 (M+H).

後処理

  1. customThe solvent was removed under vacuum
  2. additionThe residue was treated with water
  3. customsonicated briefly
  4. additionto disperse the solids
  5. customsonicated again
  6. filtrationThe solids were filtered
  7. washwashed with cold water and air
  8. customdried at room temperature
  9. customto get a clear solution
  10. temperatureThe solution was cooled to room temperature
  11. customThe solids formed
  12. filtrationwere filtered
  13. washwashed with DCM
  14. customdried under vacuum at room temperature

出典と根拠

ORDレコード
ord-0431fa96c50e4e57af851bc014d998ab
出典データセット
uspto-grants-2014_04
特許番号
US08697887B2

反応ノート

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