Sodium Hydroxide → HCID 66914263, compound

HRID 2104671Notes

Reaction equation

HRID 2104671 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[O:31][C:32](=[O:43])[C:33]1[CH:38]=[CH:37][C:36]([CH2:39]Br)=[C:35]([O:41][CH3:42])[CH:34]=1.[OH-].[Na+]>C1COCC1.CO>[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][CH2:39][C:36]1[CH:37]=[CH:38][C:33]([C:32]([OH:43])=[O:31])=[CH:34][C:35]=1[O:41][CH3:42])=[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

5

Reactant 3

HCID 14798Sodium HydroxideHCID 2759828Methyl 4-(bromomethyl)-3-methoxybenzoateHCID 11773771[4-(3-Hydroxyphenyl)-8-(Trifluoromethyl)Quinolin-3-yl](Phenyl)Methanone

Product 1

HCID 66914263HCID 66914263, compound

Reagents, catalysts & solvents 1

HCID 21899815MeOH tetrahydrofuranSolvent

Procedure

The title compound was prepared from [4-(3-hydroxyphenyl)-8-(trifluoromethyl)-quinolin-3-yl](phenyl)methanone and 4-Bromomethyl-3-methoxy-benzoic acid methyl ester following the procedure of Example 478 then hydrolysis using sodium hydroxide in THF:MeOH (1:2) at RT for 12 hr, the reaction mixture was acidified and concentrated. The crude residue was purified by reverse phase HPLC to provide the desired compound: mp 100-110° C.; MS (ES) m/z 555.8; HRMS: calcd for C32H22F3NO5+H+, 558.15228; found (ESI, [M+H]+), 558.154.

Workup

  1. customhydrolysis
  2. customat RT
  3. customfor 12 hr
  4. concentrationconcentrated
  5. customThe crude residue was purified by reverse phase HPLC

Sources & evidence

ORD record
ord-a9e92db6f22f46cb900acbce7195929e
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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