Triethylamine → HCID 66913850, compound

HRID 2104673Notes

Reaction equation

HRID 2104673 reaction equation
[OH:1][C:2]1[CH:3]=[C:4]([C:8]2[C:17]3[C:12](=[C:13]([C:18]([F:21])([F:20])[F:19])[CH:14]=[CH:15][CH:16]=3)[N:11]=[CH:10][C:9]=2[C:22]([C:24]2[CH:29]=[CH:28][CH:27]=[CH:26][CH:25]=2)=[O:23])[CH:5]=[CH:6][CH:7]=1.[C:30]([C:33]1[CH:34]=[C:35](B(O)O)[CH:36]=[CH:37][CH:38]=1)([OH:32])=[O:31].C(N(CC)CC)C>ClCCl.C([O-])(=O)C.[Cu+2].C([O-])(=O)C>[C:22]([C:9]1[CH:10]=[N:11][C:12]2[C:17]([C:8]=1[C:4]1[CH:3]=[C:2]([CH:7]=[CH:6][CH:5]=1)[O:1][C:37]1[CH:38]=[C:33]([CH:34]=[CH:35][CH:36]=1)[C:30]([OH:32])=[O:31])=[CH:16][CH:15]=[CH:14][C:13]=2[C:18]([F:21])([F:19])[F:20])(=[O:23])[C:24]1[CH:25]=[CH:26][CH:27]=[CH:28][CH:29]=1

Participants

6

Reactant 3

HCID 8471TriethylamineHCID 27339573-Carboxyphenylboronic acidHCID 11773771[4-(3-Hydroxyphenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)Methanone

Product 1

HCID 66913850HCID 66913850, compoundYield 21%

Reagents, catalysts & solvents 2

HCID 8895Cupric acetateCatalystHCID 6344DichloromethaneSolvent

Procedure

To [4-(3-hydroxy-phenyl)-8-trifluoromethylquinolin-3-yl]-phenyl methanone (0.1 g, 0.00025 mole) and 3-carboxyphenyl boronic acid (0.12 g, 0.00072 mole) in 2 ml dichloromethane was added copper acetate (0.091 g, 0.0005 mole) and triethylamine (0.1 ml, 0.00072 mole). This mixture was stirred at room temperature overnight. The reaction was then filtered and the filtrate evaporated to dryness. The crude product was purified by flash chromatography to give 0.027 g of 3-[3-(3-benzoyl-8-trifluoromethyl-quinolin-4-yl)-phenoxy]-benzoic acid: MS: MS (ESI) m/z 514; MS (ESI) m/z 512.

Workup

  1. filtrationThe reaction was then filtered
  2. customthe filtrate evaporated to dryness
  3. customThe crude product was purified by flash chromatography

Sources & evidence

ORD record
ord-ec10ee177e3243699ae6f00f372e86f8
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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