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Phenyl N-[2-(pyridin-2-ylmethyloxy)pyridin-5-yl]carbamate → 1-[2-(Pyridin-2-ylmethyloxy)pyridin-5-ylcarbamoyl]-5trifluoromethylindoline

HRID 427736
ノート
印刷プレビュー

反応式

HRID 427736 の反応式
[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16](=[O:24])OC2C=CC=CC=2)=[CH:11][N:10]=1.[F:25][C:26]([F:37])([F:36])[C:27]1[CH:28]=[C:29]2[C:33](=[CH:34][CH:35]=1)[NH:32][CH2:31][CH2:30]2>CN(C)C=O>[N:1]1[CH:6]=[CH:5][CH:4]=[CH:3][C:2]=1[CH2:7][O:8][C:9]1[CH:14]=[CH:13][C:12]([NH:15][C:16]([N:32]2[C:33]3[C:29](=[CH:28][C:27]([C:26]([F:25])([F:36])[F:37])=[CH:35][CH:34]=3)[CH2:30][CH2:31]2)=[O:24])=[CH:11][N:10]=1
参加物反応条件実験手順後処理出典と根拠反応ノート

参加物

4

反応物 2

HCID 11141770Phenyl N-[2-(pyridin-2-ylmethyloxy)pyridin-5-yl]carbamateHCID 154477895-(trifluoromethyl)-2,3-dihydro-1H-indole

生成物 1

HCID 108355851-[2-(Pyridin-2-ylmethyloxy)pyridin-5-ylcarbamoyl]-5trifluoromethylindoline収率 31.1%

試薬・触媒・溶媒 1

HCID 6228Dimethylformamide溶媒

反応条件

温度
100 °C

実験手順

Phenyl N-[2-(pyridin-2-ylmethyloxy)pyridin-5-yl] carbamate (D3, 0.20 g, 0.62 mmol) in dry dimethylformamide (10 ml) was treated with 5-trifluoromethylindoline (D6, 0.12 g, 0.62 mmol) and heated at 100° C. for 1 hour. After cooling to ambient temperature, the solvent was removed in vacuo. The residue was dissolved in dichloromethane, washed with 10% aqueous sodium hydroxide solution, dried (Na2SO4) and evaporated in vacuo. The resulting oil was chromatographed on silica gel eluting with 2% methanol/dichloromethane and triturated with diethyl ether to afford the title compound (0.08 g, 31%) as an off-white solid.

後処理

  1. temperatureAfter cooling to ambient temperature
  2. customthe solvent was removed in vacuo
  3. dissolutionThe residue was dissolved in dichloromethane
  4. washwashed with 10% aqueous sodium hydroxide solution
  5. dry with materialdried (Na2SO4)
  6. customevaporated in vacuo
  7. customThe resulting oil was chromatographed on silica gel eluting with 2% methanol/dichloromethane
  8. customtriturated with diethyl ether

出典と根拠

ORDレコード
ord-ca76e47d15cd479baf33ce92fcdccf81
出典データセット
uspto-grants-2001_11
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US06313145B1

反応ノート

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