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Hydrochloric Acid → [3-({[4-Bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-yl]oxy}methyl)phenyl]boronic acid

HRID 1626964
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HRID 1626964 반응식
[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][C:12]([CH3:15])([CH3:14])[CH3:13])[C:6]=2[CH:5]=[CH:4][C:3]=1[OH:16].Br[CH2:18][C:19]1[CH:20]=[C:21]([B:25]([OH:27])[OH:26])[CH:22]=[CH:23][CH:24]=1.C(=O)([O-])[O-].[Cs+].[Cs+].[NH4+].[Cl-].Cl>CN(C=O)C.CCOCC>[Br:1][C:2]1[C:10]2[N:9]=[N:8][N:7]([CH2:11][C:12]([CH3:13])([CH3:15])[CH3:14])[C:6]=2[CH:5]=[CH:4][C:3]=1[O:16][CH2:18][C:19]1[CH:20]=[C:21]([B:25]([OH:27])[OH:26])[CH:22]=[CH:23][CH:24]=1
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참가 물질

8

반응물 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 27732813-(Bromomethyl)benzeneboronic acidHCID 574249954-bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol

생성물 1

HCID 67888636[3-({[4-Bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-yl]oxy}methyl)phenyl]boronic acid

시약·촉매·용매 2

HCID 3283Diethyl Ether용매HCID 6228Dimethylformamide용매

실험 절차

4-Bromo-1-(2,2-dimethylpropyl)-1H-1,2,3-benzotriazol-5-ol (Example 1-2) (704 mg, 2.478 mmol, 1.0 equiv.), 3-bromomethylphenylboronic acid (11) (639 mg, 2.97 mmol, 1.2 equiv.) and cesium carbonate (969 mg, 2.97 mmol, 1.2 equiv.) were suspended in anhydrous DMF (6043 μl). The reaction mixture was stirred at room temperature overnight. The reaction mixture was diluted with Et2O, and acidified with aqueous saturated NH4Cl and HCl (1N) to pH 2. The organic layer was dried over MgSO4, filtered and concentrated to provide the titled compound. LRMS m/z (M+H) 418.0 and 420.0 (intensity ratio ˜1:1) found, 418.1 and 420.1 required.

후처리

  1. dry with materialThe organic layer was dried over MgSO4
  2. filtrationfiltered
  3. concentrationconcentrated

출처 및 근거

ORD 기록
ord-a60e253b4baf4d7f818a01676dc41701
출처 데이터셋
uspto-grants-2014_07
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US08785481B2

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