Potassium Carbonate → HCID 18412756, compound

HRID 992483Notes

Reaction equation

HRID 992483 reaction equation
[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([OH:23])=[C:6]([C:8]2([OH:22])[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:21])[CH:7]=1.[F:24][C:25]([F:35])([F:34])[C:26]1[CH:33]=[CH:32][C:29]([CH2:30]Br)=[CH:28][CH:27]=1.C([O-])([O-])=O.[K+].[K+]>CC(=O)CC>[Cl:1][C:2]1[CH:3]=[CH:4][C:5]([O:23][CH2:30][C:29]2[CH:28]=[CH:27][C:26]([C:25]([F:24])([F:34])[F:35])=[CH:33][CH:32]=2)=[C:6]([C:8]2([OH:22])[C:16]3[C:11](=[CH:12][C:13]([C:17]([F:20])([F:19])[F:18])=[CH:14][CH:15]=3)[NH:10][C:9]2=[O:21])[CH:7]=1

Participants

5

Reactant 3

HCID 11430Potassium CarbonateHCID 1230621-(Bromomethyl)-4-(trifluoromethyl)benzeneHCID 9906124HCID 9906124, compound

Product 1

HCID 18412756HCID 18412756, compoundYield 60%

Reagents, catalysts & solvents 1

HCID 6569Methyl Ethyl KetoneSolvent

Conditions

Temperature
77.5 °C

Procedure

To a solution of (±)-3-(5-chloro-2-hydroxyphenyl)-1,3-dihydro-3-hydroxy-6-(trifluoromethyl)-2H-indole-2-one (Preparation 5, 80 mg, 0.233 mmol) in 2-butanone (3mL), was added 4-(trifluoromethyl) benzyl bromide (61 mg, 0.256 mmol), K2CO3 (32 mg, 0.233 mmol) and a catalytic amount of KI. The reaction mixture was heated at 75-80° C. for 2 days. The reaction mixture was then filtered and the filtrate was concentrated in vacuo. The resulting crude product was purified by preparative HPLC to afford the title compound (70 mg, 60% yield); MS m/e 500 (M−H)−.

Workup

  1. filtrationThe reaction mixture was then filtered
  2. concentrationthe filtrate was concentrated in vacuo
  3. customThe resulting crude product was purified by preparative HPLC

Sources & evidence

ORD record
ord-7dbd171f683845dc9fcef2c6607935ee
Source dataset
uspto-grants-2002_10
Patent number
US06469042B1

Reaction notes

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