Hydrochloric Acid → HCID 66914310, compound

HRID 2104681Notes

Reaction equation

HRID 2104681 reaction equation
[CH2:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:23]=[CH:22][CH:21]=[C:20](Br)[CH:19]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[C:25]([F:28])([F:27])[F:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.[C:29]([CH2:32][CH2:33][C:34]1[CH:39]=[CH:38][C:37](B(O)O)=[CH:36][CH:35]=1)([OH:31])=[O:30].C(=O)([O-])[O-].[Na+].[Na+].Cl>COCCOC.O>[CH2:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[C:18]1[CH:19]=[C:20]([C:37]3[CH:38]=[CH:39][C:34]([CH2:33][CH2:32][C:29]([OH:31])=[O:30])=[CH:35][CH:36]=3)[CH:21]=[CH:22][CH:23]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[C:25]([F:28])([F:27])[F:26])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

7

Reactant 4

HCID 313Hydrochloric AcidHCID 10340Sodium CarbonateHCID 38634844-(2-Carboxyethyl)benzeneboronic acidHCID 669135743-Benzyl-4-(3-bromophenyl)-8-(trifluoromethyl)quinoline

Product 1

HCID 66914310HCID 66914310, compoundYield 70%

Reagents, catalysts & solvents 2

HCID 962WaterSolventHCID 80711,2-DimethoxyethaneSolvent

Procedure

To a solution of 3-benzyl-4-(3-bromophenyl)-8-(trifluoromethyl)quinoline (0.30 g, 0.7 mmol), 4-(2-carboxyethyl) benzene boronic acid (0.15 g, 0.75 mmol) in 15 ml DME under a nitrogen atmosphere is added terakistriphenyl phosphine palladium (0.08 g, 0.07 mmol) followed by sodium carbonate (0.22 g, 2.04 mmol) dissolved in 5 ml water. The reaction mixture was heated to reflux for 12 hr. The reaction was cooled, poured into 1N HCl and extracted with EtOAc. The organic layer was dried and concentrated to provide the title compound as a tan solid (0.24 g, 70%): MS (ES) m/z 509.9; HRMS: calcd for C32H24F3NO2+H+, 512.18319; found (ESI, [M+H]+), 512.1842;

Workup

  1. temperatureThe reaction mixture was heated
  2. temperatureto reflux for 12 hr
  3. temperatureThe reaction was cooled
  4. extractionextracted with EtOAc
  5. customThe organic layer was dried
  6. concentrationconcentrated

Sources & evidence

ORD record
ord-2c89f57f6e6a4f8099af00d1fff3dc7a
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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