Ethyl Bromide → HCID 67966666, compound

HRID 536198Notes

Reaction equation

HRID 536198 reaction equation
[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][NH:20][C:19](=[O:23])[CH:18]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:24]([F:27])([F:26])[F:25].[H-].[Na+].Br[CH2:31][CH3:32]>CN(C)C=O>[Cl:1][C:2]1[CH:7]=[CH:6][C:5]([O:8][C:9]2[CH:14]=[CH:13][C:12]([CH2:15][O:16][C:17]3[CH:22]=[CH:21][N:20]([CH2:31][CH3:32])[C:19](=[O:23])[CH:18]=3)=[CH:11][CH:10]=2)=[CH:4][C:3]=1[C:24]([F:27])([F:25])[F:26]

Participants

5

Reactant 3

HCID 6332Ethyl BromideHCID 24758Sodium hydrideHCID 67958516HCID 67958516, compound

Product 1

HCID 67966666HCID 67966666, compoundYield 69.5%

Reagents, catalysts & solvents 1

HCID 6228DimethylformamideSolvent

Procedure

To a solution of 4-{[(4-{[4-chloro-3-(trifluoromethyl)phenyl]oxy}phenyl)methyl]oxy}-2(1H)-pyridinone (80 mg, 0.202 mmol) in N,N-dimethylformamide (1 mL) was added Sodium hydride (80 mg, 2.00 mmol). After stirring at rt for 10 min, bromoethane (100 μL, 1.34 mmol) was added. The reaction mixture was warmed to 80° C. and stirred for 1 h, then cooled to rt, quenched by addition of methanol, concentrated. Purification via Biotage-Qs system afforded the title product (59.5 mg) as a white solid. LC-MS (ESI): m/z 424 [M+H]+; 3.76 min (ret time).

Workup

  1. temperatureThe reaction mixture was warmed to 80° C.
  2. stirringstirred for 1 h
  3. temperaturecooled to rt
  4. customquenched by addition of methanol
  5. concentrationconcentrated
  6. customPurification via Biotage-Qs system

Sources & evidence

ORD record
ord-6f678a938dd2469780cb8591da060d1f
Source dataset
uspto-grants-2014_10
Patent number
US08859573B2

Reaction notes

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