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

HRID 929183노트

반응식

HRID 929183 반응식
[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

참가 물질

5

반응물 3

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

생성물 1

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

시약·촉매·용매 1

HCID 702Ethanol용매

실험 절차

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).

후처리

  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

출처 및 근거

ORD 기록
ord-4ac2d1b3f27d407988d93f89fb8a9da0
출처 데이터셋
uspto-grants-2016_03
특허 번호
US09290517B2

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