Allyl bromide → 5-(biphenyl-4-yl)-6-chloro-2-(methylsulfonyl)-1-(prop-2-en-1-yl)-1H-benzimidazole

HRID 340768노트

반응식

HRID 340768 반응식
[C:1]1([C:21]2[CH:26]=[CH:25][CH:24]=[CH:23][CH:22]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:19]([Cl:20])=[CH:18][C:10]3[NH:11][C:12]([S:14]([CH3:17])(=[O:16])=[O:15])=[N:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1.C(=O)([O-])[O-].[K+].[K+].[CH2:33](Br)[CH:34]=[CH2:35]>C1COCC1>[C:1]1([C:21]2[CH:22]=[CH:23][CH:24]=[CH:25][CH:26]=2)[CH:6]=[CH:5][C:4]([C:7]2[C:19]([Cl:20])=[CH:18][C:10]3[N:11]([CH2:35][CH:34]=[CH2:33])[C:12]([S:14]([CH3:17])(=[O:15])=[O:16])=[N:13][C:9]=3[CH:8]=2)=[CH:3][CH:2]=1

참가 물질

5

반응물 3

HCID 7841Allyl bromideHCID 11430Potassium CarbonateHCID 684868865-biphenyl-4-yl-6-chloro-2-(methylsulfonyl)-1H-benzimidazole

생성물 1

HCID 866743305-(biphenyl-4-yl)-6-chloro-2-(methylsulfonyl)-1-(prop-2-en-1-yl)-1H-benzimidazole

시약·촉매·용매 1

HCID 8028Tetrahydrofuran용매

반응 조건

온도
60 °C

실험 절차

To a solution of 5-biphenyl-4-yl-6-chloro-2-(methylsulfonyl)-1H-benzimidazole (1.72 g, 4.49 mmol) in THF (30 ml) and 1M potassium carbonate (3.10 g, 22.46 mmol) was added allyl bromide (0.6 ml, 6.89 mmol). The reaction mixture was heated to 60° C. for 20 h. Then the volatiles were removed in vacuo and the resulting residue was partitioned between EtOAc and water. The aqueous phase was separated and extracted with EtOAc. The combined organic layers were washed with brine, dried (MgSO4), filtered, and concentrated. Chromatography of the resulting residue over silica eluting with 20-40% EtOAc/hexanes afforded the desired product. LC-MS: calculated for C23H19ClN2O2S 422.09, observed m/e: 422.94 (M+H)+ (Rt 2.52/4 min).

후처리

  1. customThen the volatiles were removed in vacuo
  2. customthe resulting residue was partitioned between EtOAc and water
  3. customThe aqueous phase was separated
  4. extractionextracted with EtOAc
  5. washThe combined organic layers were washed with brine
  6. dry with materialdried (MgSO4)
  7. filtrationfiltered
  8. concentrationconcentrated

출처 및 근거

ORD 기록
ord-0d3968ba877f42ec9f191199549538eb
출처 데이터셋
uspto-grants-2014_11
특허 번호
US08895596B2

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