Hydrochloric Acid → HCID 67888636, compound

HRID 1626964Notes

Reaction equation

HRID 1626964 reaction equation
[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

Participants

8

Reactant 5

HCID 313Hydrochloric AcidHCID 10796Cesium carbonateHCID 25517Ammonium ChlorideHCID 27732813-(Bromomethyl)benzeneboronic acidHCID 57424995HCID 57424995, compound

Product 1

HCID 67888636HCID 67888636, compound

Reagents, catalysts & solvents 2

HCID 3283Diethyl EtherSolventHCID 6228DimethylformamideSolvent

Procedure

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.

Workup

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

Sources & evidence

ORD record
ord-a60e253b4baf4d7f818a01676dc41701
Source dataset
uspto-grants-2014_07
Patent number
US08785481B2

Reaction notes

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