Cesium carbonate → Methyl 3-[(3-{[3-Benzyl-8-(Trifluoromethyl)Quinolin-4yl]Methyl}Phenoxy)Methyl]Benzoate

HRID 2104799Notes

Reaction equation

HRID 2104799 reaction equation
[CH2:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[CH2:18][C:19]1[CH:20]=[C:21]([OH:25])[CH:22]=[CH:23][CH:24]=1)=[CH:15][CH:14]=[CH:13][C:12]=2[C:26]([F:29])([F:28])[F:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1.Br[CH2:31][C:32]1[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=1)[C:35]([O:37][CH3:38])=[O:36].C([O-])([O-])=O.[Cs+].[Cs+]>C(#N)C>[CH2:1]([C:8]1[CH:9]=[N:10][C:11]2[C:16]([C:17]=1[CH2:18][C:19]1[CH:20]=[C:21]([CH:22]=[CH:23][CH:24]=1)[O:25][CH2:31][C:32]1[CH:33]=[C:34]([CH:39]=[CH:40][CH:41]=1)[C:35]([O:37][CH3:38])=[O:36])=[CH:15][CH:14]=[CH:13][C:12]=2[C:26]([F:28])([F:29])[F:27])[C:2]1[CH:7]=[CH:6][CH:5]=[CH:4][CH:3]=1

Participants

5

Reactant 3

HCID 10796Cesium carbonateHCID 517981Methyl 3-(bromomethyl)benzoateHCID 669138793-{[3-Benzyl-8-(Trifluoromethyl)Quinolin-4-yl]Methyl}Phenol

Product 1

HCID 66914384Methyl 3-[(3-{[3-Benzyl-8-(Trifluoromethyl)Quinolin-4yl]Methyl}Phenoxy)Methyl]BenzoateYield 50.9%

Reagents, catalysts & solvents 1

HCID 6342AcetonitrileSolvent

Procedure

3-{[3-Benzyl-8-(trifluoromethyl)quinolin-4-yl]methyl}phenol (0.100 g, 0.254 mmol), methyl 3-bromomethylbenzoate (0.058 g, 0.254 mmol) and Cs2CO3 (0.331 g, 1.02 mmol) in acetonitrile (4 mL) are stirred 18 h. The reaction is filtered and then purified using Prep HPLC (10 to 100% acetonitrile/water gradient) to afford 0.070 g of the title compound as a colorless oil. 1H NMR (CDCl3) δ 8.96 (s, 1H), 8.12 (d, J=8.6 Hz, 1H), 8.02 (m, 2H), 7.97 (d, J=7.7 Hz, 1H), 7.5 (m, 2H), 7.42 (m, 1H), 7.18 (m, 6H), 6.80 (dd, J=8.2 and 2.0 Hz, 1H), 6.63 (d, J=7.7 Hz, 1H), 6.51 (s, 1H), 4.96 (s, 2H), 4.45 (s, 2H), 4.19 (s, 2H), 3.92 (s, 3H).

Workup

  1. filtrationThe reaction is filtered
  2. custompurified

Sources & evidence

ORD record
ord-b3062f7052ef4757af894ac38d56c90f
Source dataset
uspto-grants-2009_08
Patent number
US07576215B2

Reaction notes

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