Ethylenediamine → 3-Fluoro-4-(2-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy)benzenamine

HRID 2117137ノート

反応式

HRID 2117137 の反応式
[F:1][C:2]1[CH:3]=[C:4]([NH2:32])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[N:15](COCC[Si](C)(C)C)[C:16]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)=[CH:17][C:10]=12.[F-].C([N+](CCCC)(CCCC)CCCC)CCC.NCCN>C1COCC1>[F:1][C:2]1[CH:3]=[C:4]([NH2:32])[CH:5]=[CH:6][C:7]=1[O:8][C:9]1[CH:14]=[CH:13][N:12]=[C:11]2[NH:15][C:16]([C:18]3[CH:19]=[N:20][CH:21]=[CH:22][CH:23]=3)=[CH:17][C:10]=12

参加物

5

反応物 3

HCID 3301EthylenediamineHCID 2724141Tetrabutylammonium FluorideHCID 210816043-Fluoro-4-(2-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy)benzenamine

生成物 1

HCID 210816053-Fluoro-4-(2-(pyridin-3-yl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy)benzenamine収率 92.1%

試薬・触媒・溶媒 1

HCID 8028Tetrahydrofuran溶媒

反応条件

温度
65 °C

実験手順

A mixture of 3-fluoro-4-(2-(pyridin-3-yl)-1-((2-(trimethylsilyl)ethoxy)methyl)-1H-pyrrolo[2,3-b]pyridin-4-yloxy)benzenamine (275 mg, 0.61 mmol), tetrabutylammonium fluoride (1 M in THF, 4 mL), and 1,2-diaminoethane (0.2 mL) in THF (4 mL) was heated at 65° C. for 24 h. The solvent was removed in vacuo. The residue was purified by flash column chromatography (silica gel, 5% MeOH/EtOAc) to afford the desired product (180 mg, 92%) as a yellow solid. LC/MS(ESI+) m/z 321 (M+H)+.

後処理

  1. customThe solvent was removed in vacuo
  2. customThe residue was purified by flash column chromatography (silica gel, 5% MeOH/EtOAc)

出典と根拠

ORDレコード
ord-f13b428896984d4ebae87fa471e5bb94
出典データセット
uspto-grants-2008_10
特許番号
US07439246B2

反応ノート

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