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Ammonium Chloride → 3-fluoro-4-(2-(1-(methoxymethyl)-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)aniline

HRID 418624
ノート
印刷プレビュー

反応式

HRID 418624 の反応式
[F:1][C:2]1[CH:25]=[C:24]([N+:26]([O-])=O)[CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]=[CH:16][N:17]([CH2:19][O:20][CH3:21])[CH:18]=3)[S:13][C:6]=12.[Cl-].[NH4+]>CCO.O.[Fe]>[F:1][C:2]1[CH:25]=[C:24]([CH:23]=[CH:22][C:3]=1[O:4][C:5]1[CH:10]=[CH:9][N:8]=[C:7]2[CH:11]=[C:12]([C:14]3[N:15]=[CH:16][N:17]([CH2:19][O:20][CH3:21])[CH:18]=3)[S:13][C:6]=12)[NH2:26]
参加物実験手順後処理出典と根拠反応ノート

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 587902607-(2-Fluoro-4-nitrophenoxy)-2-(1-(methoxymethyl)-1H-imidazol-4-yl)thieno[3,2-b]pyridine

生成物 1

HCID 587902243-fluoro-4-(2-(1-(methoxymethyl)-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yloxy)aniline収率 100%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 702Ethanol溶媒
HCID 962
Water
溶媒

実験手順

To a suspension of 94 (132 mg, 0.33 mmol) in EtOH (7 ml) and water (3 ml) was added ammonium chloride (16 mg, 0.9 eq, 0.3 mmol) and Fe (157 mg, 8.5 eq, 0.28 mmol) and the reaction mixture was heated to reflux for 2 hours. The reaction mixture was cooled to RT, filtered through celite then concentrated. The mixture was partitioned between DCM/water and the DCM was collected, dried over anhydrous sodium sulfate, filtered and concentrated. Crude 95 was used directly in the next step (122 mg, 100% yield). MS (m/z): 371.1 (M+H).

後処理

  1. temperaturethe reaction mixture was heated
  2. temperatureto reflux for 2 hours
  3. filtrationfiltered through celite
  4. concentrationthen concentrated
  5. customThe mixture was partitioned between DCM/water
  6. customthe DCM was collected
  7. dry with materialdried over anhydrous sodium sulfate
  8. filtrationfiltered
  9. concentrationconcentrated

出典と根拠

ORDレコード
ord-8628a0f6e551452db7e9a96189f1050b
出典データセット
uspto-grants-2012_01
DOI
10.6084/m9.figshare.5104873.v1
特許番号
US08093264B2

反応ノート

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