Ammonium Chloride → 2-Fluoro-N1-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yl)benzene-1,4-diamine

HRID 418712ノート

反応式

HRID 418712 の反応式
[F:1][C:2]1[CH:7]=[C:6]([N+:8]([O-])=O)[CH:5]=[CH:4][C:3]=1[NH:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:18]=[C:19]([C:21]3[N:22]=[CH:23][N:24]([CH3:26])[CH:25]=3)[S:20][C:13]=12.[NH4+].[Cl-]>CO.O.[Fe]>[F:1][C:2]1[CH:7]=[C:6]([NH2:8])[CH:5]=[CH:4][C:3]=1[NH:11][C:12]1[CH:17]=[CH:16][N:15]=[C:14]2[CH:18]=[C:19]([C:21]3[N:22]=[CH:23][N:24]([CH3:26])[CH:25]=3)[S:20][C:13]=12

参加物

6

反応物 2

HCID 25517Ammonium ChlorideHCID 59457676N-(2-Fluoro-4-nitrophenyl)-2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-amine

生成物 1

HCID 594577422-Fluoro-N1-(2-(1-methyl-1H-imidazol-4-yl)thieno[3,2-b]pyridin-7-yl)benzene-1,4-diamine収率 136.4%

試薬・触媒・溶媒 3

HCID 23925Iron触媒HCID 887Methanol溶媒HCID 962Water溶媒

実験手順

To a stirred suspension of nitro compound 338 (370 mg, 1.00 mmol) in a mixture of MeOH (20 mL) and water (10 mL) were added iron powder (280 mg, 5.01 mmol) and NH4Cl (107 mg, 2.00 mmol). The reaction mixture heated to reflux for 2 hrs, cooled down to room temperature, filtered through Celite, and rinsed with methanol. The filtrate was concentrated, diluted a bit with methanol, precipitated with AcOEt/hexanes to afford title compound 339 (463 mg, quantitative yield, ammonium salt) as a yellow solid. MS (m/z): 340.0 (M+H)+.

後処理

  1. temperatureThe reaction mixture heated
  2. temperatureto reflux for 2 hrs
  3. filtrationfiltered through Celite
  4. washrinsed with methanol
  5. concentrationThe filtrate was concentrated
  6. additiondiluted a bit with methanol
  7. customprecipitated with AcOEt/hexanes

出典と根拠

ORDレコード
ord-01e0f8c0b332411088c1b5e3ba7a954c
出典データセット
uspto-grants-2012_01
特許番号
US08093264B2

反応ノート

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