Potassium Carbonate → HCID 59627919, compound

HRID 2421227Notes

Reaction equation

HRID 2421227 reaction equation
[CH3:1][C:2]1[NH:3][C:4]2[C:9]([CH:10]=1)=[C:8]([O:11][CH2:12][C:13]1[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=1)[CH:7]=[CH:6][CH:5]=2.Br[C:20]1[CH:25]=[CH:24][C:23]([OH:26])=[C:22]([F:27])[CH:21]=1.C(=O)([O-])[O-].[K+].[K+]>CN1CCCC1=O.[Cu](I)I>[F:27][C:22]1[CH:21]=[C:20]([N:3]2[C:4]3[C:9](=[C:8]([O:11][CH2:12][C:13]4[CH:18]=[CH:17][CH:16]=[CH:15][CH:14]=4)[CH:7]=[CH:6][CH:5]=3)[CH:10]=[C:2]2[CH3:1])[CH:25]=[CH:24][C:23]=1[OH:26]

Participants

6

Reactant 3

HCID 11430Potassium CarbonateHCID 27249814-Bromo-2-fluorophenolHCID 19372290HCID 19372290, compound

Product 1

HCID 59627919HCID 59627919, compound

Reagents, catalysts & solvents 2

HCID 83717Copper iodideCatalystHCID 13387N-methyl-2-pyrrolidoneSolvent

Conditions

Temperature
190 °C

Procedure

To a solution of 2-methyl-4-[(phenylmethyl)oxy]-1H-indole {WO9204321} (440 mg, 1.86 mmol) in N-methyl-2-pyrrolidinone (4 mL) was added 4-bromo-2-fluorophenol (0.205 mL, 1.87 mmol), copper iodide (70 mg, 0.37 mmol) and potassium carbonate (641 mg, 4.64 mmol). The reaction mixture was heated in a Biotage Initiator™ Microwave Synthesizer at 190° C. for 6 hours. The mixture was filtered through a pad of Celite which was subsequently washed with ethyl acetate. The ethyl acetate solution was washed with water, dried over magnesium sulfate, filtered and then concentrated in vacuo. The product was purified by MDAP to yield the title compound (D3) (30 mg).

Workup

  1. filtrationThe mixture was filtered through a pad of Celite which
  2. washwas subsequently washed with ethyl acetate
  3. washThe ethyl acetate solution was washed with water
  4. dry with materialdried over magnesium sulfate
  5. filtrationfiltered
  6. concentrationconcentrated in vacuo
  7. customThe product was purified by MDAP

Sources & evidence

ORD record
ord-e747288dd6934406a64cde8e821911e4
Source dataset
uspto-grants-2011_06
Patent number
US07956083B2

Reaction notes

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