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Boron tribromide → Methyl 4-[(5,6-dichloro-2-{[4-(hydroxy)-phenyl]imino}-3-methyl-2,3-dihydro-1h-benzimidazol-1-yl)methyl]benzoate

HRID 1594522
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HRID 1594522 반응식
[Cl:1][C:2]1[C:31]([Cl:32])=[CH:30][C:5]2[N:6]([CH2:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=3)[C:7](=[N:10][C:11]3[CH:16]=[CH:15][C:14]([O:17]C)=[CH:13][CH:12]=3)[N:8]([CH3:9])[C:4]=2[CH:3]=1.B(Br)(Br)Br>C(Cl)Cl>[Cl:1][C:2]1[C:31]([Cl:32])=[CH:30][C:5]2[N:6]([CH2:19][C:20]3[CH:29]=[CH:28][C:23]([C:24]([O:26][CH3:27])=[O:25])=[CH:22][CH:21]=3)[C:7](=[N:10][C:11]3[CH:16]=[CH:15][C:14]([OH:17])=[CH:13][CH:12]=3)[N:8]([CH3:9])[C:4]=2[CH:3]=1
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참가 물질

4

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HCID 25134Boron tribromideHCID 69418089Methyl 4-[(5,6-dichloro-2-{[4-(methoxy)-phenyl]imino}-3-methyl-2,3-dihydro-1h-benzimidazol-1-yl)methyl]benzoate

생성물 1

HCID 69418442Methyl 4-[(5,6-dichloro-2-{[4-(hydroxy)-phenyl]imino}-3-methyl-2,3-dihydro-1h-benzimidazol-1-yl)methyl]benzoate

시약·촉매·용매 1

HCID 6344Dichloromethane용매2회

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온도
-78 °C

실험 절차

To the title compound of Example 19 Step C (0.11 mmol, 50 mg) in CH2Cl2 (0.5 mL) cooled to −78° C. was added dropwise BBr3 (0.33 mol, 330 μL of a 1 M solution in CH2Cl2). After addition, the reaction was removed from the cold bath for 30 min, then cooled to −78° C. and diluted with MeOH. The mixture was concentrated under reduced pressure and the product was isolated by chromatography on silica eluting with 4% MeOH in CH2Cl2 as a white solid. LC-MS (ESI, Method B): 1.80 min, m/z 456.1 (M+1).

후처리

  1. additionAfter addition
  2. customthe reaction was removed from the cold bath for 30 min
  3. additiondiluted with MeOH
  4. concentrationThe mixture was concentrated under reduced pressure
  5. customthe product was isolated by chromatography on silica eluting with 4% MeOH in CH2Cl2 as a white solid
  6. custom1.80 min, m/z 456.1 (M+1)

출처 및 근거

ORD 기록
ord-0ed1f94ebad9404ca693e12e11583ad4
출처 데이터셋
uspto-grants-2007_11
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US07301036B2

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