Methyl iodide → 6-Chloro-2-(methylthio)-3H-imidazo[4,5-c]pyridine

HRID 929183ノート

反応式

HRID 929183 の反応式
[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[NH:8][C:9](=[S:11])[NH:10][C:4]=2[CH:3]=1.[OH-].[K+].I[CH3:15]>CCO>[Cl:1][C:2]1[N:7]=[CH:6][C:5]2[NH:8][C:9]([S:11][CH3:15])=[N:10][C:4]=2[CH:3]=1

参加物

5

反応物 3

HCID 6328Methyl iodideHCID 14797Potassium HydroxideHCID 900416816-chloro-1H-imidazo[4,5-c]pyridine-2(3H)-thione

生成物 1

HCID 900421086-Chloro-2-(methylthio)-3H-imidazo[4,5-c]pyridine

試薬・触媒・溶媒 1

HCID 702Ethanol溶媒

実験手順

To a stirring solution of 6-chloro-1H-imidazo[4,5-c]pyridine-2(3H)-thione (1.49 g, 8.03 mmol) and potassium hydroxide (540 mg, 9.63 mmol) in anhydrous EtOH (49.7 mL) was added iodomethane (0.50 mL, 8.03 mmol). The reaction solution was stirred at RT for 3.5 h, and then partitioned between EtOAc (64 mL) and 2N HCl (11.3 mL). The aqueous layer was separated, and the pH was adjusted to a slightly basic pH with the addition of saturated NaHCO3, followed by extraction with EtOAc (100 mL). The combined organic layers were concentrated, and dried under vacuum to afford the title compound as a solid. LC-MS: calculated for C7H6ClN3S 199.00 observed m/e: 200.04 (M+H)+ (Rt 1.12/2.0 min).

後処理

  1. custompartitioned between EtOAc (64 mL) and 2N HCl (11.3 mL)
  2. customThe aqueous layer was separated
  3. additionthe pH was adjusted to a slightly basic pH with the addition of saturated NaHCO3
  4. extractionfollowed by extraction with EtOAc (100 mL)
  5. concentrationThe combined organic layers were concentrated
  6. customdried under vacuum

出典と根拠

ORDレコード
ord-4ac2d1b3f27d407988d93f89fb8a9da0
出典データセット
uspto-grants-2016_03
特許番号
US09290517B2

反応ノート

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