Stannous chloride dihydrate → N-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamine

HRID 1969800ノート

反応式

HRID 1969800 の反応式
[CH:1]1([NH:7][C:8]2[C:9]3[CH:19]=[CH:18][NH:17][C:10]=3[N:11]=[CH:12][C:13]=2[N+:14]([O-])=O)[CH2:6][CH2:5][CH2:4][CH2:3][CH2:2]1.O.O.[Sn](Cl)Cl>CCO>[CH:1]1([NH:7][C:8]2[C:13]([NH2:14])=[CH:12][N:11]=[C:10]3[NH:17][CH:18]=[CH:19][C:9]=23)[CH2:2][CH2:3][CH2:4][CH2:5][CH2:6]1

参加物

4

反応物 2

HCID 61436Stannous chloride dihydrateHCID 58557102N-cyclohexyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-amine

生成物 1

HCID 58557425N-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamine収率 87%

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

反応条件

温度
55 °C

実験手順

To a solution of N-cyclohexyl-5-nitro-1H-pyrrolo[2,3-b]pyridin-4-amine (0.15 g, 0.57 mmol) in EtOH (10 mL) was added tin (II) chloride dihydrate (0.65 g, 2.9 mmol). The reaction mixture was heated at about 55° C. for about 1 h. The solvent was removed under reduced pressure and EtOAc (75 mL) and saturated aqueous NaHCO3 (25 mL) were added. The solid that formed was collected by vacuum filtration, washed with EtOAc (25 mL), and discarded. The filtrate was washed with saturated aqueous NaHCO3 (3×20 mL), dried over anhydrous MgSO4, filtered, and concd to give N-cyclohexyl-1H-pyrrolo[2,3-b]pyridine-4,5-diamine (0.107 g, 87%) as a brown residue: LC/MS (Table 1, Method c) Rt=1.21 min; MS m/z 231 (M+H)+.

後処理

  1. customThe solvent was removed under reduced pressure and EtOAc (75 mL) and saturated aqueous NaHCO3 (25 mL)
  2. additionwere added
  3. customThe solid that formed
  4. filtrationwas collected by vacuum filtration
  5. washwashed with EtOAc (25 mL)
  6. washThe filtrate was washed with saturated aqueous NaHCO3 (3×20 mL)
  7. dry with materialdried over anhydrous MgSO4
  8. filtrationfiltered

出典と根拠

ORDレコード
ord-25a3e11bbedd4cc7ad0f18db647444a1
出典データセット
uspto-grants-2013_04
特許番号
US08426411B2

反応ノート

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